2-(2-Phenylethyl)phenol → (4R)-4-benzyloxy-1-t-butoxycarbonyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine

HRID 743297노트

반응식

HRID 743297 반응식
[C:1]1([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH2:22]([O:29][C@H:30]1[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:32]([CH2:42]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:31]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(N(C)C)=O>[CH2:22]([O:29][C@H:30]1[CH2:34][N:33]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:32]([CH2:42][O:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:31]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

참가 물질

5

반응물 3

HCID 27490412-(2-Phenylethyl)phenolHCID 23665647Potassium tert-butoxideHCID 53856550(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine

생성물 1

HCID 53917409(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-[2-(2-phenylethyl)phenoxymethyl]pyrrolidine수율 81.3%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

Following a procedure similar to that described in Example 40(a), 200 mg of 2-(2-phenylethyl)phenol (prepared as described in Preparation 19), 124 mg of potassium t-butoxide and 500 mg of (4R)-4-benzyloxy-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine were reacted in 10 ml of dimethylacetamide. The mixture was then worked up as described in Example 40(a), and the crude product thus obtained was purified by column chromatography through silica gel, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 400 mg (yield 81%) of the title compound as a colorless oil.

후처리

  1. customthe crude product thus obtained
  2. customwas purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-dfe1bdcec63d4727ae92cbb6eaabfebd
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556864

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