Dichloromethane → (2R,4R)-Methyl 4-methoxypyrrolidine-2-carboxylate

HRID 2217475Notes

Reaction equation

HRID 2217475 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([O:10][CH3:11])[CH2:7][N:6]1C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:4].C(Cl)Cl.C(O)(C(F)(F)F)=O>O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([O:10][CH3:11])[CH2:7][NH:6]1)=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68806999(2R,4R)-4-Methoxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 28937962(2R,4R)-Methyl 4-methoxypyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask containing 3 (4.67 g, 11.6 mmol) was added a solution of CH2Cl2 (27 mL), water (0.3 mL), and TFA (3.0 mL, 38.9 mmol). The solution was stirred at RT for 3 h before concentrating under reduced pressure to reveal impure 4. MS: APCI (AP+): 160.1 (M)+.

Workup

  1. concentrationbefore concentrating under reduced pressure

Sources & evidence

ORD record
ord-e0da3dddbf684d3aa45f2199706e9c84
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

Loading…