Hydrazine → tert-butyl((1S)-3-hydrazino-1-(4-(trifluoromethyl)benzyl)propyl)carbamate

HRID 598900Notes

Reaction equation

HRID 598900 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([CH2:7][C@H:8]2[CH2:12][CH2:11]C(=O)[N:9]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:5][CH:4]=1.[NH2:25][NH2:26]>C1COCC1>[C:17]([O:16][C:14](=[O:15])[NH:9][C@@H:8]([CH2:7][C:6]1[CH:21]=[CH:22][C:3]([C:2]([F:24])([F:23])[F:1])=[CH:4][CH:5]=1)[CH2:12][CH2:11][NH:25][NH2:26])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 57950685(R)-tert-Butyl 2-(4-(trifluoromethyl)benzyl)-5-oxopyrrolidine-1-carboxylate

Product 1

HCID 57950716tert-butyl((1S)-3-hydrazino-1-(4-(trifluoromethyl)benzyl)propyl)carbamateYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-tert-Butyl 2-(4-(trifluoromethyl)benzyl)-5-oxopyrrolidine-1-carboxylate (1.46 g, 4 mmol) (prepared as shown in Scheme 15) was treated with hydrazine (0.5 mL, 16 mmol) at 50° C. in THF for 30 minutes. The mixture was partitioned between EtOAc and saturated aqueous ammonium chloride, and dried over sodium sulfate. Evaporation provided the desired product as a white amorphous solid (1.27 g, 87%). LCMS (API-ES) m/z: 276 (M-Boc+H+).

Workup

  1. customThe mixture was partitioned between EtOAc and saturated aqueous ammonium chloride
  2. dry with materialdried over sodium sulfate
  3. customEvaporation

Sources & evidence

ORD record
ord-25103e843de44c948b688f3ac14abf65
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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