Water → N-(3-{3-[3-(2-Chlorophenyl)propyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

HRID 428890Notes

Reaction equation

HRID 428890 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([N:12]1[CH2:17][CH:16]2[CH:14]([C:15]2([C:19]2[CH:20]=[C:21]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=2)[CH3:18])[CH2:13]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH3:12].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][N:12]1[CH2:13][CH:14]2[CH:16]([C:15]2([C:19]2[CH:20]=[C:21]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=2)[CH3:18])[CH2:17]1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21226445Aluminium lithium hydrideHCID 22141174N-(3-{3-[3-(2-chlorophenyl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

Product 2

HCID 222AmmoniaHCID 22141246N-(3-{3-[3-(2-Chlorophenyl)propyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamideYield 159.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-{3-[3-(2-chlorophenyl)propanoyl]-6-methyl-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 131, 100 mg, 0.231 mmol) in anhydrous tetrahydrofuran (2.5 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.25 ml, 0.25 mmol) and the reaction mixture was stirred at room temperature for 7 h. The rapidly stirred reaction mixture was treated sequentially with water (0.25 ml), sodium carbonate (250 mg) and ethyl acetate (2.5 ml). The reaction mixture was left to stir overnight and then was filtered and concentrated in vacuo. This was purified by chromatography using silica gel (2 g) eluting with ethyl acetate:hexane:0.880 ammonia (60:40:1) to afford the title compound as a colourless oil (77 mg, 80%).

Workup

  1. customThe rapidly stirred reaction mixture
  2. waitThe reaction mixture was left
  3. stirringto stir overnight
  4. filtrationwas filtered
  5. concentrationconcentrated in vacuo
  6. customThis was purified by chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-69941e4606554e71b4619928b87f9491
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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