Hydrazine hydrate (1:1) → HCID 58691171, compound

HRID 1392104Notes

Reaction equation

HRID 1392104 reaction equation
[CH:1]1([N:6]2[C@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:11]=[CH:10][CH2:9][C@@H:8]([N:19]3C(=O)C4C(=CC=CC=4)C3=O)[C:7]2=[O:30])[CH2:5][CH2:4][CH2:3][CH2:2]1.O.NN>CO>[NH2:19][C@@H:8]1[CH2:9][CH:10]=[CH:11][C@@H:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:7]1=[O:30]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58691211HCID 58691211, compound

Product 1

HCID 58691171HCID 58691171, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[(3R,7S)-1-cyclopentyl-2-oxo-7-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-yl]-1H-isoindole-1,3(2H)-dione (100 mg) in MeOH (4 ml), was added hydrazine hydrate (27 mg) at RT under N2. The mixture was allowed to stir overnight at RT. The reaction was evaporated and the residue was taken up in DCM and washed with water. The organics were dried (Na2SO4), filtered and evacuated to afford the title compound (65 mg, 96% crude yield) yellow oil. 1H NMR (300 MHz, CDCl3) δ 1.38-2.31 (m, 1H), 3.46-3.56 (m, 1H), 4.91 (d, 1H, J=8 Hz), 5.24-5.34 (m, 1H), 5.88-5.96 (m, 1H), 6.25-6.33 (m, 1H), 7.21-7.36 (m, 5H).

Workup

  1. customThe reaction was evaporated
  2. washwashed with water
  3. dry with materialThe organics were dried (Na2SO4)
  4. filtrationfiltered
  5. customevacuated

Sources & evidence

ORD record
ord-2af0dfc5a6a544bcbe40d18fb23d704f
Source dataset
uspto-grants-2008_03
Patent number
US07342007B2

Reaction notes

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