Hydrazine hydrate (1:1) → HCID 178461610, compound

HRID 2179470Notes

Reaction equation

HRID 2179470 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[NH:10][C:9]1=S)([CH3:4])([CH3:3])[CH3:2].O.[NH2:24][NH2:25]>CO>[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]1[CH2:13][C@@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@@H:11]([CH3:20])[NH:10][C:9]1=[N:24][NH2:25])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131732078tert-Butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate

Product 1

HCID 178461610HCID 178461610, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To as solution of tert-butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate (100 mg, 0.31 mmol) in methanol (3.1 mL) was added hydrazine hydrate (55%, 833 μL, 9.36 mmol). The mixture was stirred 75 min, and then concentrated. Saturated aqueous sodium bicarbonate was added, and the mixture was extracted with ethyl acetate (×3). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the crude title compound, MS 319.4 (M+1).

Workup

  1. concentrationconcentrated
  2. additionSaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted with ethyl acetate (×3)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2857474cedfb4902a7afb0d716563017
Source dataset
uspto-grants-2015_06
Patent number
US09067941B2

Reaction notes

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