Hydrazine → ((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(6-(trifluoromethyl)-2H-benzo[e][1,3]oxazin-3(4H)-yl)methanone

HRID 1747155Notes

Reaction equation

HRID 1747155 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][N:9]([C:12]([C@:14]34[CH2:21][C@H:20]([N:22]5C(=O)C6C(=CC=CC=6)C5=O)[CH2:19][C@H:15]3[O:16][CH2:17][CH2:18]4)=[O:13])[CH2:8][C:7]=2[CH:33]=1.NN>C(O)C>[NH2:22][C@@H:20]1[CH2:19][C@H:15]2[O:16][CH2:17][CH2:18][C@@:14]2([C:12]([N:9]2[CH2:8][C:7]3[CH:33]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:4]=[CH:5][C:6]=3[O:11][CH2:10]2)=[O:13])[CH2:21]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 867081552-((3aS,5S,6aR)-3a-(6-(trifluoromethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine-3-carbonyl)hexahydro-2H-cyclopenta[b]furan-5-yl)isoindoline-1,3-dione

Product 1

HCID 86708156((3aS,5S,6aR)-5-aminohexahydro-2H-cyclopenta[b]furan-3a-yl)(6-(trifluoromethyl)-2H-benzo[e][1,3]oxazin-3(4H)-yl)methanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Step D (5.39 g, 11.1 mmol, 1 eq) and hydrazine (7.1 mL, 222 mmol, 20 eq) in ethanol (60 mL) was stirred at rt 18 hours. The white solid was filtered, washed with methanol and DCM, and the filtrates concentrated. Saturated NaHCO3 was added, the aqueous extracted with DCM, the organics combined, dried over MgSO4 and concentrated to afford the product of Step E. Calculated for C17H19F3N2O3: 357.1 (M+1). found: 357.3.

Workup

  1. filtrationThe white solid was filtered
  2. washwashed with methanol and DCM
  3. concentrationthe filtrates concentrated
  4. additionSaturated NaHCO3 was added
  5. extractionthe aqueous extracted with DCM
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aaf9f4cce2fe425cb21e4075fdf669df
Source dataset
uspto-grants-2015_10
Patent number
US09150532B2

Reaction notes

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