(2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate → (2S,5R)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate

HRID 2199880Notes

Reaction equation

[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([O:14][NH:15][CH:16]1[CH2:21][NH:20][C@H:19]([C:22]#[N:23])[CH2:18][CH2:17]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([O:14][NH:15][C@H:16]1[CH2:21][NH:20][C@H:19]([C:22]#[N:23])[CH2:18][CH2:17]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 35 °C

Procedure

A suspension of (2S)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate (1:1) (XI) (13 gm, 0.0404 moles) in methanol (260 ml) was heated under reflux, with stirring, for 3 hour. The resulted suspension was allowed to cool to 35° C. and the resulting suspension filtered under suction. The solid was washed with additional methanol (2×13 ml). The solid was dried under reduced pressure (4 mm Hg), to obtain (2S,5R)-5-[(benzyloxy)amino]-2-cyanopiperidine ethanedioate (XIA) as a white solid, 7.3 gm, yield 56%.

Workup

temperaturewas heated
temperatureunder reflux
filtrationthe resulting suspension filtered under suction
washThe solid was washed with additional methanol (2×13 ml)
customThe solid was dried under reduced pressure (4 mm Hg)

Sources & evidence

ORD record: ord-a9d8c3a3f20144988e38da890ba78ef2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359353B2

Reaction notes

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