Borane → 1-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanol

HRID 1387737Notes

Reaction equation

HRID 1387737 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([N+:19]([O-:21])=[O:20])[CH:6]=1)=[O:4].COC1C=CC(CC(C)NCC2C=CC=CC=2)=CC=1.B.O1CCBN1.N[C@@H]1C2C(=CC=CC=2)C[C@@H]1O>>[Br:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([N+:19]([O-:21])=[O:20])[CH:6]=1)[OH:4]

Participants

6

Reactant 5

HCID 6331BoraneHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanolHCID 30164224-Methoxy-alpha-methyl-N-(phenylmethyl)benzeneethanamineHCID 110894102-Bromo-1-(3-nitro-4-phenylmethoxyphenyl)ethanone2×HCID 53628436CID 53628436

Product 1

HCID 114395551-(4-(Benzyloxy)-3-nitrophenyl)-2-bromoethanol

Procedure

from 2-bromo-4′-benzyloxy-3′-nitroacetophenone and 4-methoxy-α-methyl-N-(phenylmethyl)benzeneethanamine comprising the sequential steps of: (a) reducing 2-bromo-4′-benzyloxy-3′-nitroacetophenone with about one equivalent of a borane reagent in the presence of a catalytic amount of a single enantiomer of an oxazaborolidine derived from cis 1-amino-2-indanol to produce substantially enantiomerically pure α-(bromomethyl)-4-phenylmethoxy-3-nitrobenzenemethanol (FBH); (b) reducing the α-(bromomethyl)-4-phenylmethoxy-3-nitrobenzenemethanol with hydrogen in the presence of a noble metal catalyst to produce an aniline FBH2; (c) formylating the aniline with formic acid and acetic anhydride to produce a compound of formula FBH3:

Sources & evidence

ORD record
ord-3fd1cdb0a9124ab48ecc654d383dee4f
Source dataset
uspto-grants-2001_07
Patent number
US06268533B1

Reaction notes

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