Benzyl chloroformate → 1-Tert-butyl 4-methyl 4-((benzyloxycarbonylamino)methyl)piperidine-1,4-dicarboxylate

HRID 216067Notes

Reaction equation

HRID 216067 reaction equation
[NH2:1][CH2:2][C:3]1([C:16]([O:18][CH3:19])=[O:17])[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(CC)C(C)C)(C)C.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>C(Cl)Cl>[CH2:33]([O:32][C:30]([NH:1][CH2:2][C:3]1([C:16]([O:18][CH3:19])=[O:17])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])[CH2:7][CH2:8]1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 254188221-tert-Butyl 4-methyl 4-(aminomethyl)piperidine-1,4-dicarboxylate

Product 1

HCID 689923421-Tert-butyl 4-methyl 4-((benzyloxycarbonylamino)methyl)piperidine-1,4-dicarboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-tert-butyl 4-methyl 4-(aminomethyl)piperidine-1,4-dicarboxylate (0.300 g, 1.1 mmol) and N,N-diisopropylethylamine (0.229 mL, 1.32 mmol) in CH2Cl2 (5 mL) at 0° C. was added benzyl chloroformate. The reaction was stirred overnight, and then diluted with CH2Cl2 and washed with H2O and brine, dried over MgSO4, and concentrated under vacuum. The residue was purified by silica gel chromatography (EtOAc:hexanes gradient) to give the title compound in 82% yield. MS (ES+) [M+H]+=407.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel chromatography (EtOAc:hexanes gradient)

Sources & evidence

ORD record
ord-0a45ae10b5af4f04b63b42e76fd927d4
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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