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20-hydroxy-16 alpha- bromo-steroid compound, synthesis method and its uses

A technology of steroidal compounds and synthetic methods, which is applied in the field of 20-hydroxy-16α-bromo-steroidal compounds, can solve the problems of complex products and low yield of androst-16-en-3β-ol, and achieve product High yield, low reagent price, avoid serious pollution effect

Inactive Publication Date: 2007-05-16
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] It has been reported in the literature that steroid-20-hydroxyl-16-sulfonate can undergo heterolytic rearrangement to obtain androst-16-en-3β-ol, but the product is complex, and the yield of androst-16-en-3β-ol Lower (J.Org.Chem., 1970, 35, 561):

Method used

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  • 20-hydroxy-16 alpha- bromo-steroid compound, synthesis method and its uses
  • 20-hydroxy-16 alpha- bromo-steroid compound, synthesis method and its uses
  • 20-hydroxy-16 alpha- bromo-steroid compound, synthesis method and its uses

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Embodiment 1

[0033] The synthesis of embodiment 1 compound 6a

[0034]

[0035] Weigh 500mg of compound 5a and dissolve it in an appropriate amount of MeOH, add 429mg (3eq.) K 2 CO 3 The hydrolysis reaction was carried out at 43° C. for 10 hours. Concentrate to near dryness, collect the residue with ethyl acetate, wash the organic phase with saturated brine, dry over anhydrous magnesium sulfate, let it stand for 30 min, filter, spin evaporate ethyl acetate, and obtain 178 mg of compound 6a (89.2%) by column chromatography.

[0036] Compound 6a, mp 168°C, [α] 25 D +9.2 (c 0.765, CHCl 3 ); 1 H-NMR (CDCl 3 , 400MHz) δ: 0.63(s, 3H, 18-H), 0.85(s, 3H, 19-H), 3.33(m, 1H, 3-H) 3.74(m, 1H, 20-H), 4.42( m, 1H, 16-H); IR ν: 3415, 2921, 2847, 1442, 1372, 1041cm -1 ;Elemental analysis calculated value C 25 h 39 o 4 Br: C 63.15, H 8.83; found C 63.36, H 8.47.

Embodiment 2

[0037] The synthesis of embodiment 2 compound 6d

[0038]

[0039] Weighed 500 mg of compound 5d and dissolved it in 10 mL of EtOH / THF (1:1), added 22 mg (1.0 eq.) of LiOH for hydrolysis reaction, and refluxed until the raw materials disappeared. After spinning to dryness, 345 mg of compound 6d (89.9%) was obtained by column chromatography.

[0040] Compound 6d, 1 H-NMR (CD 3 OD, 300MHz) δ: 0.86(s, 3H, 19-Me), 1.02(s, 3H, 18-Me), 1.41(d, J=6.8Hz, 3H, 21-Me), 3.24(dd, J= 11.1, 4.7Hz, 1H, 12-H), 3.50(m, 1H, 3-H), 4.38(m, 1H, 20-H), 4.57(m, 1H, 16-H); IRν: 3421, 1442 , 1372, 1041cm -1 ;Elemental analysis calculated value C 21 h 35 BrO 3 : C 60.72, H 8.49; Found C 59.96, H 8.68.

Embodiment 3

[0041] The synthesis of embodiment 3 compound 6e

[0042]

[0043] Weigh 500 mg of compound 5e and dissolve it in 8 mL of MeOH, add 255 mg (1.0 eq.) of Cs 2 CO 3 Carry out hydrolysis reaction, and react at room temperature until the raw materials disappear. Concentrate to near dryness, collect the residue with ethyl acetate, wash the organic phase with saturated brine, dry over anhydrous magnesium sulfate, let it stand for 30 min, filter, rotary evaporate ethyl acetate, and obtain 298 mg of compound 6e (68.6%) by column chromatography.

[0044] Compound 6e, 1 H-NMR (CDCl 3 , 300MHz) δ: 0.75(s, 3H), 0.82(s, 3H), 1.35(d, J=5.2Hz, 3H), 3.53(m, 1H), 3.84(m, 1H), 4.54(m, 1H ), 4.81(m, 1H); elemental analysis calculated value C 21 h 33 Br 3 o 2 : C 45.27, H 5.97; Found C 45.02, H 5.63.

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Abstract

The invention discloses a new structural 20-hydroxy-16 alpha-brom-steroidal compound, synthesizing method (a, acyl hydrolysis) and application (b, fragmentation rearrangement), which comprises the following steps: adopting 20-glycolic ester-16 alpha-brom-steroidal compound as raw material to obtain 20-hydroxy-16 alpha-brom-steroidal compound; fragmenting; rearranging to obtain androste-16-olefin-3 beta-alcohol as key intermediate to synthesize pig ectohormone androste-16-olefin-3-ketone and androste-16-olefin-3 alpha-alcohol.

Description

technical field [0001] The present invention relates to a class of 20-hydroxyl-16α-bromo-steroid compounds with novel structure, their synthesis method and application. 20-hydroxyacetate-16α-bromo-steroid compounds are hydrolyzed to remove acetyl groups under alkaline conditions to obtain 20-hydroxy-16α-bromo-steroid compounds; these compounds undergo fragmentation reactions under alkaline conditions Androst-16-en-3β-ol can be obtained, which is a key intermediate for the synthesis of porcine pheromone androst-16-en-3-one and androst-16-en-3α-ol and other steroid drugs. technical background [0002] Urine of boars contains androst-16-en-3-one (1) and androst-16-en-3α-ol (2), two porcine pheromones known to induce sexual activity in sows Behavior, shorten the estrous cycle, and can be used to detect the mating reaction of pigs during artificial insemination, and improve the conception rate. It has been widely used in foreign pig industries (Journal of China Pharmaceutical Un...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00C07J1/00
Inventor 田伟生周南琰许启海林静容李伯玉
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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