Benzyl chloroformate → HCID 57753905, compound

HRID 1193372Notes

Reaction equation

HRID 1193372 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9](Cl)=[O:10])=[CH:3][CH:2]=1.[CH3:12][NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:7]([O:8][C:9]([N:13]([CH3:12])[CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:18][CH2:19]1)=[O:10])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylate

Product 1

HCID 57753905HCID 57753905, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cbz-Cl (0.393 ml, 2.8 mol, 1.2 eq.) was added to a mixture of tert-butyl 4-(methylamino)-piperidine-1-carboxylate (500 mg, 2.336 mmol, 1.0 eq.) and K2CO3 (616 mg, 4.67 mmol, 2.0 eq.) in DCM (6 ml), and the mixture was stirred for 14 hours at RT. The reaction mixture was diluted with DCM (100 ml), washed with water and sat. NaCl solution (in each case 40 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 15% ethyl acetate in hexane). Yield: 49% (400 mg, 1.149 mmol)

Workup

  1. washwashed with water and sat. NaCl solution (in each case 40 ml),
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (silica gel, 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b65f00c49c52462e8fce54ecdabc3c40
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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