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

HRID 334865Notes

Reaction equation

HRID 334865 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]=[C:16]([F:20])[C:15]=2[F:21])[CH2:11][N:10]([CH2:22][C:23]([F:26])([F:25])[F:24])[C:9]1=[O:27])(C)(C)C.[ClH:29]>CCOC(C)=O>[ClH:29].[NH2:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:15]=2[F:21])[CH2:11][N:10]([CH2:22][C:23]([F:26])([F:24])[F:25])[C:9]1=[O:27]

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-bf9211bd57174632a75351a14f608d48
Source dataset
uspto-grants-2014_11
Patent number
US08883807B2

Reaction notes

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