L-Hydroxyproline → 4-Hydroxy-L-proline methyl ester hydrochloride

HRID 1015519Notes

Reaction equation

HRID 1015519 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[C:10]([Cl:13])(=O)C>CO>[ClH:13].[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3]1

Participants

4

Reactant 2

HCID 5810L-HydroxyprolineHCID 6367Acetyl chloride

Product 1

HCID 114353194-Hydroxy-L-proline methyl ester hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid (13.1 g, 0.1 mol) in methanol (400 mL) cooled to 0° C. was added acetyl chloride (14.3 mL, 0.2 mol) over a period of 30 min. The reaction mixture was warmed to room temperature and stirred for 2 h. The volatiles were removed under reduced pressure and the residue was triturated with ether several times to get methyl (2S,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride salt as a white powder (14.5 g) in 100% yield. m/z (M+1) 145; 1H NMR (DMSO-d6) 300 MHz δ 5.7-5.5 (s (br), 1H), 4.55-4.35 (m, 2H), 3.76 (s, 3H), 3.35 (d, J=12 Hz 1H), 3.10 (d, J=12 Hz 1H), 2.25-2.0 (m, 2H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was triturated with ether several times

Sources & evidence

ORD record
ord-964c73d431ce4602b336153b684ecf23
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

Loading…