tert-butyl[(3S,5S)-5-(2-fluorophenyl)-1-(2-methylpropyl)-2-oxopiperidin-3-yl]carbamate → (3S,5S)-3-amino-5-(2-fluorophenyl)-1-(2-methylpropyl)piperidin-2-one

HRID 406545Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[CH2:13][N:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11](=[O:18])[C@@H:10]([NH:19]C(=O)OC(C)(C)C)[CH2:9]1>C(OCC)(=O)C>[NH2:19][C@H:10]1[CH2:9][C@@H:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:13][N:12]([CH2:14][CH:15]([CH3:16])[CH3:17])[C:11]1=[O:18]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of tert-butyl [(3S,5S)-5-(2-fluorophenyl)-1-(2-methylpropyl)-2-oxopiperidin-3-yl]carbamate (150 mg, 0.41 mmol) in ethyl acetate (20 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=265.1 (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-7af3ae22f6c14de0bf4b92a51615343f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754096B2

Reaction notes

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