Hydrochloric Acid → (3S,5S)-3-Amino-5-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)piperidin-2-one hydrochloride

HRID 406563Notes

Reaction equation

HRID 406563 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:14][N:13]([CH2:15][C:16]([F:19])([F:18])[F:17])[C:12](=[O:20])[C@@H:11]([NH:21]C(=O)OC(C)(C)C)[CH2:10]1.[ClH:29]>CCOC(C)=O>[ClH:29].[NH2:21][C@H:11]1[CH2:10][C@@H:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH2:14][N:13]([CH2:15][C:16]([F:19])([F:17])[F:18])[C:12]1=[O:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86665206tert-butyl[(3S,5S)-5-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)piperidin-3-yl]carbamate

Product 1

HCID 86665207(3S,5S)-3-Amino-5-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)piperidin-2-one hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl [(3S,5S)-5-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)piperidin-3-yl]carbamate (1.50 g, 3.67 mmol) in EtOAc (30 mL) at 0° C. was saturated with HCl(g) and aged for 30 min. The resulting mixture was concentrated in vacuo to give the title compound. MS: m/z=309.0 (M+1); 1H NMR (500 MHz, CD3OD) δ 7.29-7.17 (m, 3H), 4.36-4.25 (m, 2H), 4.12 (dq, 1H, J=15.1, 9.3 Hz), 3.84 (m, 1H), 3.75 (ddd, 1H, J=12.0, 5.4, 1.7 Hz), 3.64 (t, 1H, J=11.6 Hz), 2.46 (m, 1H), 2.37 (q, 1H, J=12.2 Hz).

Workup

  1. customat 0° C.
  2. concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d0bc92f37fd14bdc99f95d9f5f252042
Source dataset
uspto-grants-2014_06
Patent number
US08754096B2

Reaction notes

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