Water → tert-butyl (3S)-1-(2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 338836Notes

Reaction equation

HRID 338836 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]([N:13]2[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14]2)[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[NH2:26][NH2:27].O.C(OCC)(=O)C>C(O)C(C)C>[F:10][C:9]([F:12])([F:11])[CH:8]([N:13]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14]1)[C:5]1[CH:6]=[N:7][C:2]([NH:26][NH2:27])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9321HydrazineHCID 86707402tert-butyl (3S)-1-(1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 86707403tert-butyl (3S)-1-(2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateYield 94.1%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A solution of tert-butyl (3S)-1-(1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (5.74 g, 15.11 mmol) and anhydrous hydrazine (4.74 mL, 151.1 mmol) in i-BuOH (20 mL) in a sealed tube was stirred at 130° C. for 18 hours. After cooling to ambient temperature, water (10 mL) and ethyl acetate (30 mL) were added. The organic layer was separated, washed with saturated sodium bicarbonate and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to give tert-butyl (3S)-1-(2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (5.34 g, 94.1%) as a white foam solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f7038e6b03949ba876856d747e78356
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

Loading…