Methanol → N-[2-(4-Benzyloxyphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

HRID 1388742Notes

Reaction equation

HRID 1388742 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([OH:13])[CH2:11][NH2:12].[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](=O)[CH3:30])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CO>ClCCl>[CH2:14]([O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH:29]([NH:12][CH2:11][CH:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[OH:13])[CH3:30])=[CH:26][CH:27]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5612534-BenzyloxyphenylacetoneHCID 128143572-Amino-1-(1-benzofuran-2-yl)ethan-1-ol

Product 1

HCID 12816511N-[2-(4-Benzyloxyphenyl)-1-methylethyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This was prepared in an identical manner to the compound described in Example 2 using 2-(2-benzofuranyl)-2-hydroxyethanamine (3.51 g) and 1-(4-benzyloxyphenyl)propan-2-one (4.75 g). Chromatography of the residual oily solid on Kieselgel 60 (4% methanol in dichloromethane) gave the title compound, m.p. 111°-122°, as a 20:80 mixture of diastereoisomers.

Workup

  1. customThis was prepared in an identical manner to the compound

Sources & evidence

ORD record
ord-760d555e632147a292fcb0c96d6b567f
Source dataset
uspto-grants-1984_02
Patent number
US04432993

Reaction notes

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