Methanol → (4R)-4-Hydroxy-L-proline methyl ester

HRID 1695315Notes

Reaction equation

HRID 1695315 reaction equation
S(Cl)(Cl)=O.[OH:5][C@H:6]1[CH2:10][NH:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH3:14]O>>[CH3:14][O:12][C:11](=[O:13])[C@@H:8]1[CH2:7][C@@H:6]([OH:5])[CH2:10][NH:9]1

Participants

4

Reactant 3

HCID 887MethanolHCID 5810L-HydroxyprolineHCID 24386Thionyl Chloride

Product 1

HCID 7015125(4R)-4-Hydroxy-L-proline methyl ester

Procedure

Thionyl chloride (5.6 mL, 76.3 mmol) was added dropwise to dry methanol (76 mL) at −20° C., following by addition of trans-4-hydroxy-L-proline (5.0 g, 38.1 mmol). The resulting mixture was allowed to warm to rt and stirred for 20 h. The solvent was removed under reduced pressure, and the residue was further dried under high vacuum to provide trans-4-hydroxy-L-proline methyl ester 1 as a white solid: 1HNMR (300 MHz, DMSO-d6) δ 2.18-2.23 (m, 2H), 3.06 (m, 1H), 3.32-3.36 (m, 2H), 3.76 (s, 3H), 4.42 (br. s, 1H), 4.48 (dd, J=5.4, 8.1 Hz, 1H), 5.56 (br. s, 1H); EIMS m/z 146 ([M]++1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was further dried under high vacuum

Sources & evidence

ORD record
ord-30cb2617387a43e4bb8e9e1c190df4ea
Source dataset
uspto-grants-2012_04
Patent number
US08163736B2

Reaction notes

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