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Novel method for synthesizing Corey Lactone3-TBS (tert-Butyldimethylsilane)

A selective, primary alcohol technology, used in chemical instruments and methods, compounds of Group 4/14 elements of the periodic table, and production of bulk chemicals, etc. , the effect of mild reaction conditions

Active Publication Date: 2014-02-12
TIEN TIANJIN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Relatively simple, but the raw materials are not easy to obtain.

Method used

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  • Novel method for synthesizing Corey Lactone3-TBS (tert-Butyldimethylsilane)
  • Novel method for synthesizing Corey Lactone3-TBS (tert-Butyldimethylsilane)
  • Novel method for synthesizing Corey Lactone3-TBS (tert-Butyldimethylsilane)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 150 g (3aR, 4S, 5R, 6aS)-5-hydroxyl-4-hydroxymethylhexahydro-2H-cyclopenta[b]furan-2-one 1 was suspended in 2 liters of dichloromethane, added 237 Carmidazole, 3 grams of DMAP (4-dimethylaminopyridine), 390 grams of TBSCl (tert-butyldimethylsilyl chloride) and 600 milliliters of dichloromethane were added dropwise at 0°C, and stirred at 25-30°C for 16 hours, washed with 2L X2 saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain (3aR, 4S, 5R, 6aS)-5-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxy 340 grams of white solids of hexahydro-2H-cyclopenta[b]furan-2-one 2 were directly used for subsequent reactions. 1 H-NMR (CDCl 3 ,300MHz)δ(ppm):0.056(s,6H),0.062(s,6H),0.885(s,9H),0.901(s,9H),1.967-2.015(m,2H),2.248(m,1H ), 2.550(dd,1H), 2.670(m,1H), 2.798(m,1H), 3.543(m,2H), 4.137(q,1H), 4.934(dt,1H).

[0023] Dissolve 340 g of the solid obtained in the previous step with 3 liters of acetone, add 1 kg of LiBr.H2O and 1.5 kg of polyethylen...

Embodiment 2

[0025] 150 g (3aR, 4S, 5R, 6aS)-5-hydroxyl-4-hydroxymethylhexahydro-2H-cyclopenta[b]furan-2-one 1 was suspended in 2 liters of dichloromethane, added 237 Carmidazole, 3 grams of DMAP (4-dimethylaminopyridine), 390 grams of TBSCl (tert-butyldimethylsilyl chloride) and 600 milliliters of dichloromethane were added dropwise at 0°C, and stirred at 25-30°C for 16 hours, washed with 2L X2 saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain (3aR, 4S, 5R, 6aS)-5-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxy 340 grams of white solids of hexahydro-2H-cyclopenta[b]furan-2-one 2 were directly used for subsequent reactions. 1 H-NMR (CDCl 3 ,300MHz)δ(ppm):0.056(s,6H),0.062(s,6H), 0.885(s,9H),0.901(s,9H),1.967-2.015(m,2H),2.248(m,1H ), 2.550(dd,1H), 2.670(m,1H), 2.798(m,1H), 3.543(m,2H), 4.137(q,1H), 4.934(dt,1H).

[0026] Dissolve 340 grams of the solid obtained in the previous step with 3 liters of acetone, add 1 kg of LiBr.H2O and 1.5 kg of polyet...

Embodiment 3

[0028] 150 g (3aR, 4S, 5R, 6aS)-5-hydroxyl-4-hydroxymethylhexahydro-2H-cyclopenta[b]furan-2-one 1 was suspended in 2 liters of dichloromethane, added 237 Carmidazole, 3 grams of DMAP (4-dimethylaminopyridine), 390 grams of TBSCl (tert-butyldimethylsilyl chloride) and 600 milliliters of dichloromethane were added dropwise at 0°C, and stirred at 25-30°C for 16 hours, washed with 2L X2 saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain (3aR, 4S, 5R, 6aS)-5-tert-butyldimethylsilyloxy-4-tert-butyldimethylsilyloxy 340 grams of white solids of hexahydro-2H-cyclopenta[b]furan-2-one 2 were directly used for subsequent reactions. 1 H-NMR (CDCl 3 ,300MHz)δ(ppm):0.056(s,6H),0.062(s,6H),0.885(s,9H),0.901(s,9H),1.967-2.015(m,2H),2.248(m,1H ), 2.550(dd,1H), 2.670(m,1H), 2.798(m,1H), 3.543(m,2H), 4.137(q,1H), 4.934(dt,1H).

[0029]Dissolve 340 grams of the solid obtained in the previous step with 3 liters of acetone, add 1 kg of LiBr.H2O and 1.5 kg of polyethy...

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Abstract

The invention relates to the technical filed of prostaglandin compound synthesis, and particularly relates to a novel method for synthesizing Corey Lactone3-TBS (tert-Butyldimethylsilane). The method specifically comprises the following steps: by taking Corey Lactone as a raw material, performing disiloxanyl protection; and then, selectively removing TBS protecting groups of primary alcohol, thus obtaining the Corey Lactone3-TBS. According to the invention, the method is mild in used reaction conditions, simple to operate and cheap and accessible in raw materials, causes no adverse influence to the environment, and is suitable for large-scale production.

Description

technical field [0001] The invention relates to the technical field of synthesis of prostaglandin compounds, in particular to a new method for synthesizing Corey Lactone3-TBS. Background technique [0002] The full name of Corey Lactone3-TBS is (3aR,4S,5R,6aS)-5-tert-butyldimethylsilyloxy-4-tetrahydroxymethylhexahydro-2H-cyclopenta[b]furan-2 - Ketone. Molecular formula: C 14 h 26 o 4 Si, the structure is as follows: [0003] [0004] Corey Lactone3-TBS is an important intermediate in the synthesis of prostaglandin compounds, and there are not many synthetic literature reports. Generally, Corey Lactone is used to first protect the primary alcohol, then silicon etherify the secondary hydroxyl group, and finally remove the protecting group on the primary alcohol. Tetrahedron Letters 47 (2006) 6689 [0005] [0006] However, the removal of the trityl protecting group on the primary alcohol requires the use of expensive Et at -50 degrees 2 AlCl, the operation is also ...

Claims

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Application Information

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IPC IPC(8): C07F7/18
CPCY02P20/55
Inventor 杨波彭乐
Owner TIEN TIANJIN PHARMA
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