tert-Butylhydrazine monohydrochloride → HCID 16045164, compound

HRID 2354903Notes

Reaction equation

HRID 2354903 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]3[CH2:17][CH2:18][CH2:19][CH:12]2[C:13](=[CH:21]O)[C:14](=O)[CH2:15]3)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].Cl.[C:29]([NH:33][NH2:34])([CH3:32])([CH3:31])[CH3:30]>C(O)(=O)C>[C:29]([N:33]1[C:14]2[CH2:15][CH:16]3[N:11]([S:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)(=[O:10])=[O:9])[CH:12]([CH2:19][CH2:18][CH2:17]3)[C:13]=2[CH:21]=[N:34]1)([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 81889tert-Butylhydrazine monohydrochlorideHCID 517045Sodium AcetateHCID 668419749-(4-Chlorophenylsulfonyl)-2-(hydroxymethylene)-9-azabicyclo[3.3.1]nonan-3-one

Product 1

HCID 16045164HCID 16045164, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of the enol-ketone (9-[(4-chlorophenyl)sulfonyl]-2-(hydroxymethylene)-9-azabicyclo[3.3.1]nonan-3-one, 34 mg, 0.10 mmol), sodium acetate (41 mg, 0.5 mmol) and glacial acetic acid (0.8 mL) in a vial was added the tert-butylhydrazine hydrochloride (31 mg, 0.25 mmol) with good stirring. The vial was capped and the reaction mixture was stirred evenly and heated to 100° C. Upon complete consumption of the enol-ketone (2-18 h, LC-MS), the reaction mixture was evaporated under a stream of nitrogen while being warmed in a 90° C. bath. The brown residue was dissolved with dichloromethane and water. The organic phase was washed with 5% NaHSO4 (3×), 5% NaHCO3 (2×), and brine (2×), dried (Na2SO4), applied to a silica gel column and eluted (0-10% EtOAc in dichloromethane) to yield the product upon evaporation. MS (ES) m/e 306.0 (M+H)+.

Workup

  1. customThe vial was capped
  2. customUpon complete consumption of the enol-ketone (2-18 h, LC-MS)
  3. customthe reaction mixture was evaporated under a stream of nitrogen
  4. temperaturewhile being warmed in a 90° C. bath
  5. dissolutionThe brown residue was dissolved with dichloromethane and water
  6. washThe organic phase was washed with 5% NaHSO4 (3×), 5% NaHCO3 (2×), and brine (2×)
  7. dry with materialdried (Na2SO4)
  8. washeluted (0-10% EtOAc in dichloromethane)
  9. customto yield the product
  10. customupon evaporation

Sources & evidence

ORD record
ord-0665ef804b744faa9c1145fa5ba4b30c
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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