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

HRID 2206643Notes

Reaction equation

HRID 2206643 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 ter-butyl 4-acetylpiperidine-1-carboxylate (10 g, 44.05 mmol) in tetrahydrofuran (100 ml) and methanol (1 (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-d76b91161f544f28be3937e130d17d5d
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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