Benzyl chloroformate → Benzyl 3-pyrroline-1-carboxylate

HRID 729353Notes

Reaction equation

HRID 729353 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:6]1[CH:11]=[CH:10][C:9]([CH2:12][O:13][C:14](Cl)=[O:15])=[CH:8][CH:7]=1>C(Cl)Cl>[CH2:12]([O:13][C:14]([N:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1)=[O:15])[C:9]1[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 31268Pyrrolidine

Product 1

HCID 643471Benzyl 3-pyrroline-1-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially-obtained pyrrolidine 5 (6.7 g, 96 mmol) was dissolved in DCM (100 ml) at 0° C. Cbz-Cl (13.6 g, 80 mmol) was added slowly, and the reaction was allowed to stir for 14 hours. The solvent was removed under vacuum, and the residue was taken up in ethyl acetate. This ethyl acetate was washed with 0.5 N HCl two times, saturated sodium bicarbonate solution once, brine and dried over MgSO4. The solvent was removed under vacuum to yield the title product 6 (15.9 g (99%), 78 mmol). 1H NMR (DMSO-d6): δ 7.24 (m, 5H), 5.61 (m, 2H), 5.35 (s, 2H), 3.62 (d, J =4.3 Hz, 2H). MS (ESI-POS): [M+H]+=204.

Workup

  1. customThe solvent was removed under vacuum
  2. washThis ethyl acetate was washed with 0.5 N HCl two times, saturated sodium bicarbonate solution once
  3. dry with materialbrine and dried over MgSO4
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6f73cc4e15a946f7a7844aa8a3813df4
Source dataset
uspto-grants-2009_09
Patent number
US07582634B2

Reaction notes

Loading…