Benzyl chloroformate → 1-N-Boc-4-(N-cbz-aminomethyl)piperidine

HRID 1856647Notes

Reaction equation

HRID 1856647 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 117920261-N-Boc-4-(N-cbz-aminomethyl)piperidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2 (2.4 g, 11.8 mmol) in 60 ml of ethyl acetate was added 60 ml of saturated K2CO3. To this biphasic solution was added benzyl chloroformate (2.03 ml, 14.23 mmol) dropwise. After stirring at room temperature for 3 hours the layers were separated and the organic layer dried over MgSO4, filtered, and the solvents removed in vacuo. The crude product was purified by chromatography on silica gel (3:1 hexane:ethyl acetate) to give the title compound.

Workup

  1. customwere separated
  2. dry with materialthe organic layer dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents removed in vacuo
  5. customThe crude product was purified by chromatography on silica gel (3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-1db1c0308a744b59a60adc9dc3da9186
Source dataset
uspto-grants-2000_11
Patent number
US06143750

Reaction notes

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