(-)-Dibenzoyltartrate → 2,2-Dimethyl-propionic acid (3S,4S)-3-methyl-piperidin-4-yl ester (-)-dibenzoyltartrate

HRID 1804761Notes

Reaction equation

HRID 1804761 reaction equation
[CH3:1][CH:2]1[CH:7]([O:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][NH:4][CH2:3]1.[C:15]([C:23]([C:38]([O-:40])=[O:39])([OH:37])[C:24]([C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([OH:28])[C:25]([O-:27])=[O:26])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C>[C:29]([C:24]([C:25]([OH:27])=[O:26])([OH:28])[C:23]([C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([OH:37])[C:38]([OH:40])=[O:39])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH3:1][C@@H:2]1[C@@H:7]([O:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 21978704(-)-DibenzoyltartrateHCID 668421342,2-Dimethyl-propionic acid (3RS,4RS)-3-methyl-piperidin-4-yl ester

Product 1

HCID 1317301552,2-Dimethyl-propionic acid (3S,4S)-3-methyl-piperidin-4-yl ester (-)-dibenzoyltartrate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2,2-Dimethyl-propionic acid (3RS,4RS)-3-methyl-piperidin-4-yl ester (5) (9.6 g, 48 mmol) is dissolved in 50 ml of ethyl acetate. A solution of (−)-dibenzoyltartrate (8.6 g, 24 mmol) in ethyl acetate is added drop wise. The precipitate is filtrated off and washed with cold ethyl acetate to yield colourless crystals.

Workup

  1. filtrationThe precipitate is filtrated off
  2. washwashed with cold ethyl acetate
  3. customto yield colourless crystals

Sources & evidence

ORD record
ord-5dd345f6fc7e4ea281f841b92d6979a7
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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