Sodium Hydroxide → (3R,4R)-3-methylpiperidin-4-yl pivalate

Reaction equation

[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.[OH-].[Na+]>>[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

Reactant 2

HCID 14798Sodium Hydroxide

HCID 596002413-Methyl-4-piperidyl (3S,4S)-Pivalate

Product 1

HCID 59600263(3R,4R)-3-methylpiperidin-4-yl pivalate

Procedure

The mother liquor of 17 from above is treated with 1N-NaOH to obtain the free base which is then crystallized with D-(+)-O,O′-Dibenzoyl tartaric acid as described above to give the antipode 20.

Workup

customto obtain the free base which
customis then crystallized with D-(+)-O,O′-Dibenzoyl tartaric acid
customto give the antipode 20

Sources & evidence

ORD record: ord-6f2a25e861ee4cca9dbb627ef491ca59
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183366B2

Reaction notes

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