Benzyl chloroformate → HCID 23291373, compound

HRID 365377Notes

Reaction equation

HRID 365377 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH:12]1([CH2:17][NH2:18])[CH2:16][CH2:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:2]([NH:18][CH2:17][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 80153CyclopentanemethylamineHCID 81531Diisopropylethylamine

Product 1

HCID 23291373HCID 23291373, compoundYield 121.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (0.919 g, 5.38 mmol) was added to a solution of cyclopentylmethylamine (0.445 g, 4.49 mmol) and DIEA (1.74 g, 13.5 mmol) in 50 mL of CH2Cl2 and the mixture was strried overnight at R.T. The mixture was concentrated in vacuo and the residue was taken up in EtOAc, washed with water, sat. aq. NaHCO3, brine, dried over MgSO4 and concentrated to give the crude N-Cbz-cyclopentylmethylamine (1.275 g) which was used without further purification. 1H NMR consistent with structure.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washwashed with water, sat. aq. NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-773847fc49f745e8aec9753ca1682247
Source dataset
uspto-grants-2000_10
Patent number
US06127372

Reaction notes

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