Hydrochloric Acid → (2S,4S)-4-Fluoropyrrolidine-2-carboxamide
Reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[C:14](=[O:16])[NH2:15])=O)(C)(C)C.Cl>C(O)CCC>[F:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([C:14]([NH2:15])=[O:16])[CH2:10]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of (2S,4S)-2-carbamoyl-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester (1.0 g), conc. Hydrochoric acid (0.6 ml) and 1-butanol (10 ml) is heated for 48 hours at 50° C. The reaction mixture is evaporated and partitioned dichloromethane and aqueous sodium bicarbonate, the dichloromethane layers are dried over sodium sulphate and evaporated. A solution of 7M ammonia in methanol (10 ml) is added to the residue and the mixture is stood for 60 hours at room temperature in a sealed vessel. Evaporation and trituration with ethanol gives the title compound as a white solid.
Workup
- customThe reaction mixture is evaporated
- custompartitioned dichloromethane and aqueous sodium bicarbonate
- dry with materialthe dichloromethane layers are dried over sodium sulphate
- customevaporated
- additionA solution of 7M ammonia in methanol (10 ml) is added to the residue
- customEvaporation and trituration with ethanol
Sources & evidence
- ORD record
- ord-85643e7558e241e58340ea2fdf0a5e44
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940771B2
Reaction notes
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