P-Toluenesulfonylhydrazide → HCID 68468480, compound

HRID 218070Notes

Reaction equation

HRID 218070 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[C:16](=O)[CH:10]([CH2:11][CH:12]([C:18]([O:20][CH3:21])=[O:19])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(NN)(C1C=CC(C)=CC=1)(=O)=O.C([BH3-])#N.[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH2:16][CH:14]([CH2:13][CH:12]([C:18]([O:20][CH3:21])=[O:19])[CH2:11]2)[CH2:15]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 15303P-ToluenesulfonylhydrazideHCID 5003444Sodium cyanoborohydrideHCID 68468881HCID 68468881, compound

Product 1

HCID 68468480HCID 68468480, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(tert-butoxycarbonyl)-9-oxo-3-azabicyclo[3.3.1]nonane-7-carboxylate (14.76 g, 49.63 mmol), in anhydrous THF (250 mL) was added tosylhydrazine (11.1 g, 59.6 mmol), and the mixture was stirred for 2 h at ambient temperature. The reaction mixture was heated to 65° C., sodium cyanoborohydride (12.5 g, 198 mmol) was added, and the mixture was stirred for 16 h at 65° C. The reaction mixture was cooled to ambient temperature and concentrated by rotary evaporation. The residue was purified by flash silica gel chromatography, using an ethyl acetate in hexane gradient, to give 8.71 g (61.9% yield) of the methyl 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.1]nonane-7-carboxylate as a colorless solid (1H NMR (CDCl3): δ 3.97-3.8 (m, 2H), 3.65 (s, 3H), 2.85-2.75 (m, 2H), 2.57-2.47 (m, 1H), 2.38-2.20 (m, 2H), 2.0-1.7 (m, 4H), 1.68-1.60 (m, 1H), 1.52-1.41 (m, 1H), 1.41 (s, 9H); LC-MS (MH+): 284).

Workup

  1. temperatureThe reaction mixture was heated to 65° C.
  2. stirringthe mixture was stirred for 16 h at 65° C
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. concentrationconcentrated by rotary evaporation
  5. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-e238fd8aa10a48bb8b8ca66b907a10e4
Source dataset
uspto-grants-2012_06
Patent number
US08198296B2

Reaction notes

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