Ammonium Acetate → Tert-butyl 4-amino-3,3-dimethylpiperidine-1-carboxylate

HRID 1063309Notes

Reaction equation

C([O-])(=O)C.[NH4+].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][C:16](=O)[C:15]([CH3:21])([CH3:20])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C([BH3-])#[N:23].[Na+]>CO>[NH2:23][CH:16]1[CH2:17][CH2:18][N:13]([C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[CH2:14][C:15]1([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 25 °C

Procedure

Ammonium acetate (700 g, 9.09 mol) was added to a stirred solution of 1-t-butyloxy carbonyl-3,3-dimethyl-4-piperidone (352 g, 1.55 mol) in methanol (1.0 L). The suspension was stirred for 3 hr at 20-30° C. The reaction mixture was cooled to 0° C. and sodiumcyanoborohydride (45 g, 0.71 mol) was added portion wise over 30 minutes. Cooling was removed and the suspension was stirred for 12 hr at 20-30° C. The reaction mixture was concentrated to dryness, stirred with water (2.0 L) and extracted with 1.0 L×3 dichloromethane. Combined organic extract was washed with water and dried over sodium sulfate. Evaporation of organic solvent afforded the product.

Workup

temperatureThe reaction mixture was cooled to 0° C.
temperatureCooling
customwas removed
stirringthe suspension was stirred for 12 hr at 20-30° C
concentrationThe reaction mixture was concentrated to dryness
stirringstirred with water (2.0 L)
extractionextracted with 1.0 L×3 dichloromethane
extractionCombined organic extract
washwas washed with water
dry with materialdried over sodium sulfate
customEvaporation of organic solvent
customafforded the product

Sources & evidence

ORD record: ord-e61591f3213a46df8d6f94577f968336
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06964966B2

Reaction notes

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