Benzyl chloroformate → 4-Benzyloxycarbonylamino-1-t-butyloxycarbonyl-3,3-dimethylpiperidine

HRID 1865252Notes

Reaction equation

HRID 1865252 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C:14]1([CH3:27])[CH3:26].C([O-])(O)=O.[Na+]>O1CCCC1.O>[CH2:5]([O:4][C:2]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C:14]1([CH3:27])[CH3:26])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 10171391Tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate

Product 1

HCID 690182114-Benzyloxycarbonylamino-1-t-butyloxycarbonyl-3,3-dimethylpiperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

Benzyl chloroformate (50% in toluene, 450 ml, 1.57 mol) was added to a stirred suspension of 4-amino-1-t-butyloxycarbonyl-3,3-dimethylpiperidine (365 g) as prepared above and NaHCO3 (150 g, 1.78 mol) in dry tetrahydrofuran (1.5 L). The reaction mixture was stirred for 20 hr at 35° C. The reaction mixture was diluted with 3.5 L water and was extracted with 2.0 L×2 ethyl acetate. Combined organic extract was washed with water, dried over Na2SO4 and concentrated to dryness. The residue was subjected to chromatography on a silica gel column to give 4-benzyloxycarbonylamino-1-t-butyloxycarbonyl-3,3-dimethylpiperidine in 63% (350 g) yield. m/z 363 (M+1).

Workup

  1. extractionwas extracted with 2.0 L×2 ethyl acetate
  2. extractionCombined organic extract
  3. washwas washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a80b21614990438baefd3e3b6fd36874
Source dataset
uspto-grants-2009_12
Patent number
US07626032B2

Reaction notes

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