4-Nitrophenyl chloroformate → (3S,4S)-benzyl 4-cyclohexyl-3-((4-nitrophenoxy)carbonylamino)piperidine-1-carboxylate

HRID 1254412Notes

Reaction equation

HRID 1254412 reaction equation
[NH2:1][C@H:2]1[C@H:7]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][N:4]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:3]1.Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=1)=[O:26].C([O-])(O)=O.[Na+]>C(#N)C>[CH:8]1([C@@H:7]2[CH2:6][CH2:5][N:4]([C:14]([O:16][CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:15])[CH2:3][C@H:2]2[NH:1][C:25]([O:27][C:28]2[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=2)=[O:26])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 59382981(3S,4S)-benzyl 3-amino-4-cyclohexylpiperidine-1-carboxylate

Product 1

HCID 57544908(3S,4S)-benzyl 4-cyclohexyl-3-((4-nitrophenoxy)carbonylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3S,4S)-benzyl 3-amino-4-cyclohexylpiperidine-1-carboxylate (23 mg, 0.073 mmol), 4-nitrophenyl chloroformate (16 mg, 1.1 equiv) and powdered NaHCO3 (13 mg, 2 equiv) were mixed with acetonitrile (3 mL). The mixture was stirred 1 h at rt. LC-MS showed the reaction was complete. The reaction mixture was concentrated to afford (3S,4S)-benzyl 4-cyclohexyl-3-((4-nitrophenoxy)carbonylamino)piperidine-1-carboxylate which was used directly in the next step. LC-MS (3 min) tR=2.24 min., m/z 482 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-07d4e86f66cf4d1fb2a38f161e26aab6
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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