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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 49980Generated: October 26, 2026

Methanol → (2S,4R)-4-(4-Bromobenzyloxy)-2-methyl-proline Methyl Ester

https://huagongshe.com/reaction/49980

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantThionyl ChlorideHCID 24386—
Reactant(2S,4R)-N-Boc-4-(4-Bromobenzyloxy)-2-methyl-prolineHCID 21301005—
Product(2S,4R)-4-(4-Bromobenzyloxy)-2-methyl-proline Methyl EsterHCID 59917097—

Reaction Conditions

Temperature20 °C

Reaction Steps

SOCl2 (0.27 mL) was carefully added dropwise to 2.7 mL of MeOH at −5° C. To this mixture was added (2S,4R)-N-Boc-4-(4-Bromobenzyloxy)-2-methyl-proline (0.25 g) in 2.7 mL of MeOH. The reaction mixture was allowed to warm to 20° C. and stirred overnight. The solvent was evaporated under reduced pressure and the residue dissolved in DCM. The organic layer was washed with water, dried over MgSO4, and evaporated in vacuo to afford the titled compound (85 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06710064B2
Source datasetuspto-grants-2004_03
ORD IDord-b910daef01354485a9900e65aeddd66b
Source noteuspto-grants-2004_03