Dichloromethane → HCID 67108955, compound

HRID 222247Notes

Reaction equation

HRID 222247 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:15]([O:22][C:23]([NH:25][NH2:26])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(Cl)Cl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O.C(O)(=O)C>[CH2:15]([O:22][C:23]([NH:25][NH:26][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 79242Benzyl carbazateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67108955HCID 67108955, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a mixture of tert-butyl 4-oxopiperidine-1-carboxylate (10.0 g), benzylhydrazinecarboxylate (16.7 g), DCM (150 mL), and acetic acid (5.75 mL) was added sodium triacetoxyborohydride (31.9 g), followed by stirring at room temperature for 2.5 days. To the reaction liquid was added water, and the organic phase was separated. The aqueous phase was extracted with chloroform, and the combined organic phase was washed with water, a saturated aqueous sodium bicarbonate, and saturated brine in this order, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10) to obtain tert-butyl 4-{2-[(benzyloxy)carbonyl]hydrazino}piperidine-1-carboxylate (10.0 g).

Workup

  1. customTo the reaction liquid
  2. customthe organic phase was separated
  3. extractionThe aqueous phase was extracted with chloroform
  4. washthe combined organic phase was washed with water
  5. dry with materiala saturated aqueous sodium bicarbonate, and saturated brine in this order, and dried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10)

Sources & evidence

ORD record
ord-da855ba55dc94d989a6553767eb3dc31
Source dataset
uspto-grants-2012_06
Patent number
US08207199B2

Reaction notes

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