Lithium borohydride → (5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ol

HRID 409034

반응식

HRID 409034 반응식
[BH4-].[Li+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:21][CH2:20][C@@H:19]([O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C:12]1=[O:33]>COC1CCCC1>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C@@H:11]1[CH2:21][CH2:20][C@@H:19]([O:22][Si:23]([CH:27]([CH3:29])[CH3:28])([CH:30]([CH3:32])[CH3:31])[CH:24]([CH3:25])[CH3:26])[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[C@H:12]1[OH:33]

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 57911475(6S,9R)-6-(2,3-Difluorophenyl)-6,7,8,9-tetrahydro-9-[[tris(1-methylethyl)silyl]oxy]-5H-cyclohepta[b]pyridin-5-one

생성물 1

HCID 57911423(5S,6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ol수율 65%

시약·촉매·용매 1

HCID 138539Cyclopentyl methyl ether용매

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온도
0 °C

실험 절차

Lithium borohydride (0.982 g, 45.1 mmol) was added to a cyclopentyl methyl ether (30 mL) solution of (6S,9R)-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-one (5.0224 g, 11.27 mmol) at 0° C. under N2. The reaction mixture was stirred at 0° C. for 2 hours and then an addition 4 hours at room temperature. The reaction was quenched by adding methanol. The reaction mixture was stirred for 0.5 hour. The solvent was mostly removed via vacuum and the crude material was taken up in ethyl acetate, which was washed with water three times. Flash column by ethyl acetate in hexane from 0 to 10% gave the desired product (3.28 g, 65%).

후처리

  1. additionan addition 4 hours at room temperature
  2. customThe reaction was quenched
  3. additionby adding methanol
  4. stirringThe reaction mixture was stirred for 0.5 hour
  5. customThe solvent was mostly removed via vacuum
  6. washwhich was washed with water three times

출처 및 근거

ORD 기록
ord-613adbb88c844232aca16582d503ae0a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759372B2

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