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 406553Notes

Reaction equation

[CH3:1][C@H:2]1[N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6](=[O:12])[C@@H:5]([NH:13]C(=O)OC(C)(C)C)[CH2:4][C@H:3]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[NH2:13][C@H:5]1[CH2:4][C@@H:3]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@@H:2]([CH3:1])[N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:6]1=[O:12]

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-e3a14520264b41d28f20c71cfb9a8608
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754096B2

Reaction notes

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