Water → 1,1-Dimethylethyl (3R,4S)-3-amino-4-fluoro-1-pyrrolidinecarboxylate

HRID 2280383Notes

Reaction equation

HRID 2280383 reaction equation
[N:1]([C@H:4]1[C@@H:8]([F:9])[CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[NH2:1][C@H:4]1[C@@H:8]([F:9])[CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 131733502cis-Tert-butyl 3-azido-4-fluoropyrrolidine-1-carboxylate

Product 1

HCID 510719831,1-Dimethylethyl (3R,4S)-3-amino-4-fluoro-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a round-bottomed flask equipped with a magnetic stir bar and a reflux condenser, to a solution of cis-tert-butyl 3-azido-4-fluoropyrrolidine-1-carboxylate (86 mg, 0.374 mmol) in THF (5.5 mL) was added PPh3 on polystyrene (1.6 mmol/g, 280 mg, 0.448 mmol) and water (0.33 mL). The reaction mixture was stirred at 60° C. for 2 h. The mixture was then filtered and the filtrate dried over MgSO4 and filtered. The solvent was removed under reduced pressure to afford cis-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate as a colorless oil. LC-MS-conditions 10: tR=0.45 min; [M-CH3+H]+=190.41.

Workup

  1. filtrationThe mixture was then filtered
  2. dry with materialthe filtrate dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ad2802bbb9d043419a3e8860c216b1ae
Source dataset
uspto-grants-2015_09
Patent number
US09139524B2

Reaction notes

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