Water → HCID 22813385, compound

HRID 1732585Notes

Reaction equation

HRID 1732585 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(C)C=CC(S([N:16]2[C:32]3[C:19]4=[C:20]([CH:29]=[CH:30][CH:31]=3)[C@H:21]3[O:26][CH2:25][C:24](=O)[NH:23][C@@H:22]3[CH2:28][C:18]4=[CH:17]2)(=O)=O)=CC=1.O>O1CCCC1>[CH:29]1[C:20]2[C@H:21]3[O:26][CH2:25][CH2:24][NH:23][C@@H:22]3[CH2:28][C:18]3[C:19]=2[C:32]([NH:16][CH:17]=3)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 54168596HCID 54168596, compound

Product 1

HCID 22813385HCID 22813385, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred slurry of lithium aluminum hydride (3.0 gms) in tetrahydrofuran (200 ml) is added trans-4-(p-tolylsulphonyl)-4,6,6a,8,9,10a hexahydro-7H-indolo-[3,4-gh]-[1,4]-benzoxazin-8-one (3.0 gms) in portions over 5 minutes. The resulting mixture is refluxed for 17 hours. The cooled slurry is hydrolyzed with water (6 ml), and the organic phase is separated from the solid inorganics by filtration. The solid is rinsed with ether (3×100 ml). The organic solvents are dried over anhydrous sodium sulfate. After filtration, the solvents are removed under reduced pressure (20 mm). The resulting oil is purified by column chromatography silica; CHCl3 (sat. with NH4OH) to yield 700 mg of trans 4,6,6a,8,9,10a-Hexahydro-7H-indolo-[3,4 gh]-[1,4]-benzoxazine; which after recrystalization from methanol gives 540 mg (25%) m.p. 175°-177° C. with previous softening.

Workup

  1. temperatureThe resulting mixture is refluxed for 17 hours
  2. customthe organic phase is separated from the solid inorganics by filtration
  3. washThe solid is rinsed with ether (3×100 ml)
  4. dry with materialThe organic solvents are dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvents are removed under reduced pressure (20 mm)
  7. customThe resulting oil is purified by column chromatography silica

Sources & evidence

ORD record
ord-b4a30e87c71342ddb4052a02c6f2f8ca
Source dataset
uspto-grants-1980_12
Patent number
US04238486

Reaction notes

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