Ammonium Acetate → tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylate

HRID 1527124Notes

Reaction equation

HRID 1527124 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=O)[CH3:2].C([O-])(=O)C.[NH4+].[B-]C#[N:24].[Na+]>O1CCCC1.CO>[NH2:24][CH:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:2]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 109879834-Acetyl-piperidine-1-carboxylic acid tert-butyl esterHCID 20587905Sodium cyanoborohydride [MI]

Product 1

HCID 22647295tert-Butyl 4-(1-aminoethyl)piperidine-1-carboxylateYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-acetylpiperidine-1-carboxylate (10 g, 44.05 mmol) in tetrahydrofuran (100 ml) and methanol (100 ml) were added ammonium acetate (20 g, 264.3 mmol) and sodium cyanotrihydroborate (20 g, 264.3 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuum. The crude product was added water (100 ml), and extracted with ethyl acetate (50 mL×3). The organic layer was dried over sodium sulfate and concentrated to give tert-butyl 4-(1-aminoethyl)piperidine-1-carboxylate (6 g, yield: 60%) as a colorless liquid. LRMS (M+H+) m/z: calcd 228.15. found 229.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum
  2. additionThe crude product was added water (100 ml)
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5224e01db0e6401f92634af7e24ce670
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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