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Hydride → N-(3-{6-Methyl-3-[3-(2-thienyl)propyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide

HRID 428886
Notes
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Reaction equation

HRID 428886 reaction equation
[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([C:8](=O)[CH2:9][CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH2:6]2.[Li].[H-].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[CH3:1][C:2]1([C:17]2[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])[CH:20]=[CH:21][CH:22]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8][CH2:9][CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH2:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 166653HydrideHCID 516892Sodium BicarbonateHCID 3028194LithiumHCID 22141147N-(3-{6-methyl-3-[3-(2-thienyl)propanoyl]-3-azabicyclo[3.1.0]hex-6-yl]phenyl)methanesulfonamide

Product 1

HCID 22141228N-(3-{6-Methyl-3-[3-(2-thienyl)propyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamideYield 70.5%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-{6-methyl-3-[3-(2-thienyl)propanoyl]-3-azabicyclo[3.1.0]hex-6-yl]phenyl)methanesulfonamide (Preparation 125, 200 mg, 0.49 mmol) in anhydrous tetrahydrofluran (7.5 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium alumirnium hydride (1.0M solution in tetrahydrofuran, 0.99 ml, 0.99 mmol) and the mixture was stirred at room temperature for 2 h. The rapidly stirred reaction mixture was treated sequentially with water (1.0 ml), sodium hydrogen carbonate (1.0 g) and ethyl acetate (25 ml). After 15 min the reaction mixture was filtered and concentrated in vacuo to afford a light yellow oil. This was purified by chromatography using a Biotage Flash 12™ cartridge packed with silica gel (8 g) eluting with hexane:ethyl acetate (100:0 to 0:100) to afford the title compound as a colourless oil (135 mg, 70%).

Workup

  1. customThe rapidly stirred reaction mixture
  2. filtrationAfter 15 min the reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customto afford a light yellow oil
  5. customThis was purified by chromatography
  6. washeluting with hexane:ethyl acetate (100:0 to 0:100)

Sources & evidence

ORD record
ord-6a4dfb31312e46008212ee64940a3db9
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06313312B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes