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

HRID 2364597Notes

Reaction equation

HRID 2364597 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.C(N(C(C)C)CC)(C)C.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>ClCCl>[CH2:29]([O:28][C:26]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-(aminomethyl)piperidine-1-carboxylate (0.611 g, 2.851 mmol) and diisopropylethylamine (0.479 g, 3.706 mmol) were dissolved in 30 mls of dry dichloromethane. To this mixture was added benzyl chloroformate (0.552 g, 3.136 mmol) and the mixture was stirred at room temperature for 2 hours. The mixture was then diluted with 50 mls of dichloromethane, washed once with 1N aqueous HCl, one with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure to 950 mgs (96%) of the title compound and used directly without further purification.

Workup

  1. washwashed once with 1N aqueous HCl, one with saturated sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure to 950 mgs (96%) of the title compound
  4. customused directly without further purification

Sources & evidence

ORD record
ord-0a7e9376de244e2eb290a0b1a278c07d
Source dataset
uspto-grants-2014_04
Patent number
US08691809B2

Reaction notes

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