Sodium Acetate → tert-Butyl 4-(methylamino)piperidine-1-carboxylate

HRID 379018Notes

Reaction equation

HRID 379018 reaction equation
Cl.CN.C([O-])(=O)C.[Na+].[C:9]([BH3-])#[N:10].[Na+].[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>CO>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([NH:10][CH3:9])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Product 1

HCID 15380702tert-Butyl 4-(methylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Powdered molecular seives (3 Å, 5.2 g), methylamine hydrochloride (16.96 g, 251 mmol), anhydrous sodium acetate (41.21 g, 502 mmol), and 95% sodium cyanoborohydride (3.99 g, 60 mmol) were added sequentially to a solution of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester in methanol (400 mL) at 0° C., and the mixture was allowed to warm to 25° C. over several hours. After 18 hours at 25°C., the reaction mixture was filtered thru Celite®, the solids washed with methanol and ethyl acetate, and the filtrate concentrated. The residue was dissolved in ethyl acetate and the resulting solution washed twice with 2N NaOH, once with brine, dried and concentrated to an oil (12.79 g, 119%).

Workup

  1. filtrationthe reaction mixture was filtered thru Celite®
  2. washthe solids washed with methanol and ethyl acetate
  3. concentrationthe filtrate concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe resulting solution washed twice with 2N NaOH, once with brine
  6. customdried
  7. concentrationconcentrated to an oil (12.79 g, 119%)

Sources & evidence

ORD record
ord-3abc48a8e86d467fa0da3529b75a1505
Source dataset
uspto-grants-2001_10
Patent number
US06297269B1

Reaction notes

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