Water → Ammonia

HRID 1826393Notes

Reaction equation

HRID 1826393 reaction equation
[CH3:1][C:2]1([C:18]2[CH:19]=[C:20]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:22][CH:23]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([C:8](=O)/[CH:9]=[CH:10]/[C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH3:16])[CH2:6]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH3:5].[CH3:1][C:2]1([C:18]2[CH:19]=[C:20]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:22][CH:23]=2)[CH:7]2[CH:3]1[CH2:4][N:5]([CH2:8]/[CH:9]=[CH:10]/[C:11]1[S:12][CH:13]=[CH:14][C:15]=1[CH3:16])[CH2:6]2

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21226445Aluminium lithium hydrideHCID 22141297HCID 22141297, compound

Product 2

HCID 222AmmoniaHCID 22141141HCID 22141141, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3-{6-methyl-3-[(E)-3-(3-methyl-2-thienyl)-2-propenoyl]-3-azabicyclo[3.1.0]hex-6-yl}phenyl)methanesulfonamide (Preparation 134, 100 mg, 0.240 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 very pale yellow oil (60 mg, 62%).

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-fede0368afeb4a9bb6fd504681780405
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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