Benzyl chloroformate → HCID 18698055, compound

HRID 2289533Notes

Reaction equation

HRID 2289533 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]1[CH2:23][CH2:22][CH:21]([C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])[CH2:20]1)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:9]([N:19]1[CH2:23][CH2:22][CH:21]([C:24]([O:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:25])[CH2:20]1)([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 13969058HCID 13969058, compound

Product 1

HCID 18698055HCID 18698055, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylchloroformate (2.86 ml) was added to a stirred suspension of N-benzyl-3-n-butoxy carbonyl pyrrolidine (1.75 g) and sodium bicarbonate (2.52 g) in dichloromethane (30 ml). The reaction was stirred for 0.5 hours, filtered and the filtrate evaporated to give an oil. The residual oil was purified by chromatography on silica gel; elution with ethyl acetate/hexane (1/9 v/v) gave, as a pale yellow oil, N-Cbz-3-n-butoxycarbonyl pyrrolidine (1.40 g);

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated
  3. customto give an oil
  4. customThe residual oil was purified by chromatography on silica gel
  5. washelution with ethyl acetate/hexane (1/9 v/v)

Sources & evidence

ORD record
ord-9342945eb95741bbb1e6936b5c4aa68f
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

Loading…