Ammonium Acetate → tert-Butyl 4-amino-3-methoxypiperidine-1-carboxylate

HRID 2168196Notes

Reaction equation

HRID 2168196 reaction equation
[CH3:1][O:2][CH:3]1[C:8](=O)[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]1.C([BH3-])#[N:18].[Na+].C([O-])(=O)C.[NH4+]>CO>[NH2:18][CH:8]1[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][CH:3]1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 57363786tert-Butyl 3-methoxy-4-oxopiperidine-1-carboxylate

Product 1

HCID 53396191tert-Butyl 4-amino-3-methoxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-(methyloxy)-4-oxo-1-piperidinecarboxylate D18 (2.9 g) in MeOH (100 ml), was added sodium cyanoborohydride (7.9 g, 126 mmol) and ammonium acetate (9.7 g, 126 mmol) at R.T. The reaction mixture was stirred for 4 hours. The resulting mixture was concentrated in vacuo, dissolved in water, basified with sodium hydroxide to pH10 and extracted with DCM. The organic layer was dried over anhydrous MgSO4, concentrated in vacuo to get the desired product D19 in 2.85 g. LCMS [MH+] [email protected] min (5 min run)

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. dissolutiondissolved in water
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-39b0db23f22f48d08747b3ea32266c1e
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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