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

HRID 340175Notes

Reaction equation

HRID 340175 reaction equation
[CH3:1][C@H:2]1[NH:7][C:6](=S)[C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4][C@H:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.[NH2:24][NH2:25]>CO>[C:12]([O:11][C:10](=[O:16])[NH:9][C@H:5]1[CH2:4][C@@H:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:2]([CH3:1])[NH:7][C:6]1=[N:24][NH2:25])([CH3:15])([CH3:14])[CH3:13]

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 a 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-5ebec1c3ab7246979feb70424d737011
Source dataset
uspto-grants-2014_11
Patent number
US08895572B2

Reaction notes

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