Sodium cyanoborohydride → HCID 68468480, compound

HRID 1620507Notes

Reaction equation

HRID 1620507 reaction equation
O=[C:2]1[CH:7]2[CH2:8][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH:3]1[CH2:4][N:5]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6]2.C([BH3-])#N.[Na+]>C1COCC1>[CH:3]12[CH2:2][CH:7]([CH2:8][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:10]1)[CH2:6][N:5]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:4]2

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 68468881HCID 68468881, compound

Product 1

HCID 68468480HCID 68468480, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-tert-butyl 7-methyl 9-oxo-3-azabicyclo[3.3.1]nonane-3,7-dicarboxylate (22.1 g) in THF (372 mL) was added p-toluenesulfonylhydrazide (16.6 g). The reaction mixture was stirred at room temperature for 2 hr, sodium cyanoborohydride was added. The mixture was stirred at 65° C. for 16 hr, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (9.50 g).

Workup

  1. stirringThe mixture was stirred at 65° C. for 16 hr
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f6a5f007cef348b3b1f27191ab013089
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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