Methanol → HCID 53420628, compound

HRID 1042882Notes

Reaction equation

HRID 1042882 reaction equation
[F:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[F:1][CH:2]1[CH2:6][NH:5][CH:4]([C:7]([O:9][CH3:14])=[O:8])[CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 11902999(4R)-4-Fluoro-L-proline

Product 1

HCID 53420628HCID 53420628, compound

Conditions

Temperature
0 °C

Procedure

A round bottom flask was charged with (2S,4R)-4-fluoropyrrolidine-2-carboxylic acid (300 mg, 2254 μmol) and 22 mL MeOH. The heterogeneous mixture was cooled to 0° C. under nitrogen, and thionyl chloride (181 μl, 2479 μmol) was added dropwise. The reaction mixture was allowed to warm slowly to RT, and stirring was continued overnight at 65° C. The mixture was concentrated under high vacuum to provide methyl 4-fluoropyrrolidine-2-carboxylate hydrochloride as a mixture of the (2S,4R) and (2R,4R) diastereomers, confirmed by 1H and 13C NMR.

Workup

  1. temperatureto warm slowly to RT
  2. concentrationThe mixture was concentrated under high vacuum

Sources & evidence

ORD record
ord-5e0aac0cf4934e92b84e581a09a71f30
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

Loading…