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. HCl (0.6 ml) and 1-butanol (10 ml) was heated for 48 h at 50° C. The RM was evaporated and partitioned DCM and aqueous NaHCO3, the DCM layers were dried over Na2SO4 and evaporated. A solution of 7 M ammonia in methanol (10 ml) was added to the residue and the mixture was stood for 60 h at it in a sealed vessel. Evaporation and trituration with EtOH gave the title compound as a white solid.
Workup
- customThe RM was evaporated
- custompartitioned DCM and aqueous NaHCO3
- dry with materialthe DCM layers were dried over Na2SO4
- customevaporated
- additionA solution of 7 M ammonia in methanol (10 ml) was added to the residue
- customEvaporation and trituration with EtOH
Sources & evidence
- ORD record
- ord-b2baecee795e41b28667368393a6836c
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357707B2
Reaction notes
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