Sodium cyanoborohydride → (2S)-2-(benzyloxycarbonylamino)-4-(1-(tert-butoxycarbonyl)-3,3-dimethylpiperidin-4-ylamino)butanoic acid

HRID 408021Notes

Reaction equation

[CH3:1][C:2]1([CH3:16])[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[NH2:17][CH2:18][CH2:19][C@H:20]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[C:21]([OH:23])=[O:22].[BH3-]C#N.[Na+]>C1COCC1.O>[CH2:28]([O:27][C:25]([NH:24][C@@H:20]([CH2:19][CH2:18][NH:17][CH:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][C:2]1([CH3:16])[CH3:1])[C:21]([OH:23])=[O:22])=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a 0° C. solution of tert-butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate (1.76 g, 7.74 mmol) and (S)-4-amino-2-(benzyloxycarbonylamino)butanoic acid (1.95 g, 7.74 mmol) in THF (20 mL) and water (3 mL) was added NaCNBH3 (0.48 g, 7.7 mmol). This mixture was stirred at 60° C. for 2 days. The reaction was then evaporated to a solid to give the crude (2S)-2-(benzyloxycarbonylamino)-4-(1-(tert-butoxycarbonyl)-3,3-dimethylpiperidin-4-ylamino)butanoic acid. This material was taken on directly to the next step.

Workup

customThe reaction was then evaporated to a solid

Sources & evidence

ORD record: ord-5911e8e4e85d4e4984f77f11c707b034
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754226B2

Reaction notes

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