Water → N-(3-{3-[3-(3,4-Dichlorophenyl)propyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

HRID 428881Notes

Reaction equation

HRID 428881 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([N:13]2[CH2:18][CH:17]3[CH:15]([C:16]3([C:20]3[CH:21]=[C:22]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=[CH:24][CH:25]=3)[CH3:19])[CH2:14]2)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:13]2[CH2:18][CH:17]3[CH:15]([C:16]3([C:20]3[CH:21]=[C:22]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=[CH:24][CH:25]=3)[CH3:19])[CH2:14]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 22141281N-(3-{3-[3-(3,4-dichlorophenyl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

Product 1

HCID 22141269N-(3-{3-[3-(3,4-Dichlorophenyl)propyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamideYield 19.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-{3-[3-(3,4-dichlorophenyl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 119, 30 mg, 0.06 mmol) in anhydrous tetrahydrofuran (1 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuiran, 0.12 ml, 0.12 mmol) and the mixture was stirred at room temperature for 3 h. The rapidly stirred reaction mixture was treated sequentially with water (0.12 ml), sodium hydrogen carbonate (200 mg) and ethyl acetate (10 ml). After 30 min the reaction mixture was filtered and concentrated in vacuo to give a colourless oil. This was purified by preparative HPLC (condition 8) to afford the title compound as a pale yellow oil (5.2 mg, 19%).

Workup

  1. customThe rapidly stirred reaction mixture
  2. filtrationAfter 30 min the reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customto give a colourless oil
  5. customThis was purified by preparative HPLC (condition 8)

Sources & evidence

ORD record
ord-7e71354b2e924ddcb702155601fe58b3
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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