Sodium Bicarbonate → tert-Butyl trans(+/-)-4-amino-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

HRID 1425009Notes

Reaction equation

HRID 1425009 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C@H:5]1[NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[N+]=[N-].[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.CO.O.O.[Ni](Cl)Cl>[NH2:1][C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C@H:5]1[NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86648551tert-Butyl trans(+/-)-4-azido-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

Product 1

HCID 86648550tert-Butyl trans(+/-)-4-amino-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 10942802Nickel chloride dihydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl trans(±)-4-azido-3-{[benzyloxy)carbonyl]amino}piperidine-1-carboxylate obtained in Example (79b) (265.6 mg, 0.71 mmol) was dissolved in THF (6 mL) and methanol (3 mL). Nickel chloride dihydrate (345 mg, 1.42 mmol) and sodium borohydride (117 mg, 2.85 mmol) were added under ice-cooling, and the mixture was heated to room temperature and stirred for 30 minutes. Saturated aqueous sodium bicarbonate solution was added to the reaction solution, followed by filtration through celite and extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.

Workup

  1. temperaturecooling
  2. filtrationfollowed by filtration through celite and extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-4a9ba0712850420a9916aa1f29b9198a
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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