2-(2-(3-Methoxyphenyl)ethyl)phenol → (R)-1-t-Butoxycarbonyl-2-{2-[2-(3-methoxyphenyl) ethyl]phenoxymethyl}pyrrolidine

HRID 743320Notes

Reaction equation

HRID 743320 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].[C:24]([O:28][C:29]([N:31]1[CH2:35][CH2:34][CH2:33][C@@H:32]1[CH2:36]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:30])([CH3:27])([CH3:26])[CH3:25]>CC(N(C)C)=O>[C:24]([O:28][C:29]([N:31]1[CH2:35][CH2:34][CH2:33][C@@H:32]1[CH2:36][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 105854482-(2-(3-Methoxyphenyl)ethyl)phenolHCID 11760051(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 53745429(R)-1-t-Butoxycarbonyl-2-{2-[2-(3-methoxyphenyl) ethyl]phenoxymethyl}pyrrolidineYield 85.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 40(a), 1.00 g of 2-[2-(3-methoxyphenyl)ethyl]phenol (prepared as described in Preparation 20), 0.740 g of potassium t-butoxide and 2.33 g of (R)-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 1.54 g (yield 85%) 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-46a6cea55b9646ab8b2a1be06b83fdd9
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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