Hydrazine hydrate (1:1) → HCID 22721250, compound

HRID 1582397Notes

Reaction equation

HRID 1582397 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][C:13]([N:15]1[CH2:21][CH:20]2[N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:17]([CH2:18][CH2:19]2)[CH2:16]1)=[O:14].O.NN>CCO>[NH2:3][CH2:12][C:13]([N:15]1[CH2:16][CH:17]2[N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:20]([CH2:19][CH2:18]2)[CH2:21]1)=[O:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22721236HCID 22721236, compound

Product 1

HCID 22721250HCID 22721250, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of tert-Butyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl]-3,8-diazabicyclo[3.2.1]octane-8-carboxylate (70.0 mg, 0.187 mmol) in EtOH (1.9 mL) was added hydrazine monohydrate (19.0 mg, 0.375 mmol) at room temperature and the mixture was refluxed for 1 h. After cooling, the precipitates formed were filtered off. The filtrate was evaporated in vacuo and the residue was purified by preparative TLC (SiO2, 20×20 cm, 1 mm, CH2Cl2/MeOH/aqueous NH3=92/6/2) to afford a product (21.4 mg, 42%) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. temperatureAfter cooling
  3. customthe precipitates formed
  4. filtrationwere filtered off
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by preparative TLC (SiO2, 20×20 cm, 1 mm, CH2Cl2/MeOH/aqueous NH3=92/6/2)

Sources & evidence

ORD record
ord-05b30a40325845c786443ad9f57af785
Source dataset
uspto-grants-2004_05
Patent number
US06734306B2

Reaction notes

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