4-Methylmorpholine → tert-Butyl 4-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylate

HRID 417946Notes

Reaction equation

HRID 417946 reaction equation
[OH: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.CN1CCOCC1.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:25]>C(Cl)Cl>[C:24](=[O:25])([O:26][C:27]1[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=1)[O: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

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 57955467tert-Butyl 4-((((4-nitrophenoxy)carbonyl)oxy)methyl)piperidine-1-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (36.1 g, 168 mmol) and NMM (20 mL, 182 mmol) in DCM (500 mL) at 0° C. was added p-nitrophenyl chloroformate (33.9 g, 168 mmol). The reaction mixture was stirred at room temperature overnight and then washed sequentially with 1M aq HCl (500 mL), sat aq NaHCO3 solution (3×500 mL), dried (MgSO4) and concentrated in vacuo to give (1-(tert-butoxy-carbonyl)piperidin-4-yl)methyl 4-nitrophenyl carbonate (61.2 g, 96%) as a yellow solid.

Workup

  1. washwashed sequentially with 1M aq HCl (500 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3cde7f58fd714ab8907f4dd971355786
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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