tert-Butyl [(3S,5S,6R)-6-methyl-1-(2-methylpropyl)-2-oxo-5-phenylpiperidin-3-yl]carbamate → (3S,5S,6R)-3-amino-6-methyl-1-(2-methylpropyl)-5-phenylpiperidin-2-one

HRID 448231Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[N:10]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:9]1=[O:25])(C)(C)C>C(OCC)(=O)C>[NH2:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@@H:11]([CH3:20])[N:10]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:9]1=[O:25]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of tert-butyl[(3S,5S,6R)-6-methyl-1-(2-methylpropyl)-2-oxo-5-phenylpiperidin-3-yl]carbamate (140 mg, 0.39 mmol) in ethyl acetate (10 mL), pre-cooled to 0° C. was sparged with HCl gas for ˜1 min. The ice-bath was removed and the acidic solution was allowed to warm to 23° C. as stirring was continued for 2 h. The mixture was then concentrated to dryness to afford the title compound as a hydrochloride salt. MS: m/z=261.3 (M+1).

Workup

customwas sparged with HCl gas for ˜1 min
customThe ice-bath was removed
concentrationThe mixture was then concentrated to dryness

Sources & evidence

ORD record: ord-551614d04cc741a3b62e54f94c382b82
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481556B2

Reaction notes

Loading…