2-Acetylpyridine → (1S)-2-(methylamino)-1-pyridin-2-ylethanol

HRID 23704

Reaction equation

[CH3:1][NH:2][CH2:3][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[OH:5].C1(C)C=CC(S(N[C@@H](C2C=CC=CC=2)[C@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.C(C1C=CC=CN=1)(=O)C>>[CH3:1][NH:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[OH:5]

Participants

Reactant 3

HCID 142862-Acetylpyridine

HCID 6612782(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine

HCID 10149007(R)-2-(methylamino)-1-pyridin-2-ylethanol

Product 1

HCID 39235348(1S)-2-(methylamino)-1-pyridin-2-ylethanol

Procedure

As described for the preparation of (1R)-2-(methylamino)-1-pyridin-2-ylethanol (Preparations 65-69), using (1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine in place of (1R,2R)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine, 2-acetylpyridine was converted to the title compound, isolated as an amber oil.

Sources & evidence

ORD record: ord-c8b3f6c9228c4dc4a40f7101196bea11
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Linked notes

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