Hydrazine → HCID 11683136, compound

HRID 1178850Notes

Reaction equation

HRID 1178850 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][O:7][CH2:8][C@@:9]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:13][CH2:12][C@@H:11]([N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:10]1.NN>C1(C)C=CC=CC=1>[F:1][C:2]([F:38])([F:39])[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH2:6][O:7][CH2:8][C@@:9]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:13][CH2:12][C@@H:11]([NH2:14])[CH2:10]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58592529HCID 58592529, compound

Product 1

HCID 11683136HCID 11683136, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-((1R,3S)-3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclopentyl)isoindoline-1,3-dione (113 mg), available from Example 7, in toluene (0.83 mL) was added anhydrous hydrazine (66 μL), and the reaction mixture was heated at 80° C. for 12 h. The precipitate was removed by filtration, and the filtrate was evaporated in vacuo to give the title compound (80 mg). The 1H NMR data is identical to that of its (1S,3R) isomer shown in Example 6. HRMS m/z calcd for C21H22F6NO (M+H)+ 418.1607. found 546.1619.

Workup

  1. customThe precipitate was removed by filtration
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-67237eca125d404993e1c610b29e3c50
Source dataset
uspto-grants-2007_10
Patent number
US07276631B2

Reaction notes

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