tert-Butyl carbazate → Benzyl 4-[2-(tert-butoxycarbonyl)hydrazinyl]piperidine-1-carboxylate

HRID 1351414Notes

Reaction equation

HRID 1351414 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[C:18]([O:22][C:23]([NH:25][NH2:26])=[O:24])([CH3:21])([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[C:18]([O:22][C:23]([NH:25][NH:26][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 70091tert-Butyl carbazateHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 11573844Benzyl 4-[2-(tert-butoxycarbonyl)hydrazinyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

Benzyl 4-oxo-1-piperidinecarboxylate (10.0 g, 42.9 mmol), tert-butyl-1-hydrazinecarboxylate (5.70 g, 42.9 mmol) and sodium triacetoxyborohydride (13.6 g, 64.1 mmol) were stirred together for 4 hours at room temperature in dichloromethane/acetic acid (40 ml, 10% solution). The solvents were evaporated under reduced pressure. The residue was basified with saturated sodium carbonate solution and extracted with ethyl acetate. The combined organic solutions were dried (MgSO4), filtered and evaporated under reduced pressure to yield the title compound as a colourless gum, 14.2 g.

Workup

  1. customThe solvents were evaporated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic solutions were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-62a05c04978a461d8916bc376882fd3c
Source dataset
uspto-grants-2007_05
Patent number
US07217714B1

Reaction notes

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