Water → HCID 22141304, compound

HRID 1826387Notes

Reaction equation

HRID 1826387 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[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+]>O1CCCC1.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][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:27])=[O:28])[CH:22]=[CH:23][CH:24]=2)[CH3:18])[CH2:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 22141240HCID 22141240, compound

Product 1

HCID 22141304HCID 22141304, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-{3-[3-(1-benzofuran-2-ylcarbonyl)-6-methyl-3-azabicyclo[3.1.0]hex-6-yl]phenyl}methanesulfonamide (Preparation 127, 200 mg, 0.487 mmol) in anhydrous tetrahydrofuran (5 ml) under a nitrogen atmosphere at 0° C. was added dropwise lithium aluminium hydride (1.0M solution in tetrahydrofuran, 0.97 ml, 0.97 mmol) and the reaction mixture was stirred at room temperature overnight. The rapidly stirred reaction mixture was treated sequentially with water (1.0 ml), sodium hydrogen carbonate (1.0 g) and ethyl acetate (15 ml). After 5 min, the reaction mixture was filtered and concentrated in vacuo to afford 180 mg of a pale 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 over 30 min) then ethyl acetate:methanol (100:0 to 0:100 over 15 min) to afford the title compound as a white foam (136 mg, 70%).

Workup

  1. customThe rapidly stirred reaction mixture
  2. waitAfter 5 min
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-687aec4fd1074a37b05630e9d8b43668
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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