2-[2-(3-Methylphenyl)ethyl]phenol → (4R)-4-benzyloxy-1-t-butoxycarbonyl-2-{2-[2-(3-methylphenyl)ethyl]phenoxymethyl}pyrrolidine

HRID 743302Notes

Reaction equation

HRID 743302 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].[CH2:23]([O:30][C@H:31]1[CH2:35][N:34]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH:33]([CH2:43]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:32]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(N(C)C)=O>[CH2:23]([O:30][C@H:31]1[CH2:35][N:34]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH:33]([CH2:43][O:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[CH2:32]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 106323412-[2-(3-Methylphenyl)ethyl]phenolHCID 23665647Potassium tert-butoxideHCID 53856550(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine

Product 1

HCID 54190298(4R)-4-benzyloxy-1-t-butoxycarbonyl-2-{2-[2-(3-methylphenyl)ethyl]phenoxymethyl}pyrrolidineYield 59.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 40(a), 400 mg of 2-[2-(3-methylphenyl)ethyl]phenol (prepared as described in Preparation 25), 232 mg of potassium t-butoxide and 870 mg of (4R)-4-benzyloxy-1-t-butoxycarbonyl-2-(p-toluenesulfonyloxymethyl)pyrrolidine were reacted in 25 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 560 mg (yield 59%) of the title compound as a colorless oil.

Workup

  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

Sources & evidence

ORD record
ord-c47f3ad802524ec0a405efe4452dc6ed
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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