Benzyl chloroformate → HCID 18698055, compound

HRID 2288745Notes

Reaction equation

HRID 2288745 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+]>C(Cl)Cl>[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 CH2Cl2 (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 EtOAc/150.C6H14 (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 EtOAc/150

Sources & evidence

ORD record
ord-f281ea5779434a1f8a490dbaf962e1ca
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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