Pyridine → N-[(1Z)-{(E,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-2-oxoindene-3-ylidene}methyl]-N-phenethylacetamide

HRID 1922638Notes

Reaction equation

HRID 1922638 reaction equation
[Br:1]/[CH:2]=[C:3]1/[C@H:4]2[C@:8]([CH3:12])([CH2:9][CH2:10][CH2:11]/1)/[C:7](=[CH:13]/[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:6](=[O:21])[CH2:5]2.[C:22](Cl)(=[O:24])[CH3:23].N1C=CC=[CH:28][CH:27]=1>>[Br:1]/[CH:2]=[C:3]1\[CH2:11][CH2:10][CH2:9][C@@:8]2([CH3:12])[C@H:4]\1[CH2:5][C:6](=[O:21])/[C:7]/2=[CH:13]\[N:14]([CH2:15][CH2:16][C:17]1[CH:28]=[CH:27][CH:20]=[CH:19][CH:18]=1)[C:22](=[O:24])[CH3:23]

Participants

4

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 67493986(1Z,3aR,4E,7aS)-4-(bromomethylene)-hexahydro-7a-methyl-1-{(phenylamino)methylene}-1H-indene-2(3H)-one2×

Product 1

HCID 59456519N-[(1Z)-{(E,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-2-oxoindene-3-ylidene}methyl]-N-phenethylacetamideYield 91%

Procedure

To a solution of (1Z,3aR,4E,7aS)-4-(bromomethylene)-hexahydro-7a-methyl-1-{(phenylamino)methylene}-1H-indene-2(3H)-one (Compound 27: 182 mg, 0.486 mmol) in pyridine (1 ml), acetyl chloride (50 μl, 0.703 mmol) was added at 0° C. The resulting mixture was allowed to rise to room temperature and stirred for 30 minutes. The solvent was removed by evaporator, and the residue was dissolved in diethyl ether. The resulting mixture was washed with 2 N hydrochloric acid, water and with saturated brine, and dried over magnesium sulfate, followed by evaporation under reduced pressure to obtain a crude product of N-[(1Z)-{(E,3aS,7aR)-7-(bromomethylene)-octahydro-3a-methyl-2-oxoindene-3-ylidene}methyl]-N-phenethylacetamide (184 mg, 91%).

Workup

  1. customto rise to room temperature
  2. customThe solvent was removed by evaporator
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washThe resulting mixture was washed with 2 N hydrochloric acid, water and with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-e3c2656129154a0e9a6eaa48550227b4
Source dataset
uspto-grants-2012_05
Patent number
US08173824B2

Reaction notes

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