Water → HCID 22813386, compound

HRID 1732587Notes

Reaction equation

HRID 1732587 reaction equation
C1(C)C=CC(S([N:10]2[C:27]3[C:13]4=[C:14]([CH:24]=[CH:25][CH:26]=3)[C@H:15]3[O:20][CH2:19][C:18](=O)[N:17]([CH3:22])[C@@H:16]3[CH2:23][C:12]4=[CH:11]2)(=O)=O)=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[CH3:22][N:17]1[C@@H:16]2[CH2:23][C:12]3[C:13]4[C:27]([NH:10][CH:11]=3)=[CH:26][CH:25]=[CH:24][C:14]=4[C@H:15]2[O:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22813389HCID 22813389, compound

Product 1

HCID 22813386HCID 22813386, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of trans-4-(p-tolylsulphonyl)-4,6,6a,8,9,10a-hexahydro-7-methyl-7H-indolo-[3,4 gh]-[1,4]-benzoxazin-8-one (3.0 gms; 0.008 m) and lithium aluminum hydride (3.0 gm; 0.08 m) in tetrahydrofuran (200 ml) is refluxed for 17 hours. The cooled solution is hydrolyzed with water (6 ml). The solid is filtered, and the organic solvent is dried over anhydrous sodium sulfate. After filtration, the solvent is removed under reduced pressure (20 mm). The gum is crystallized from methanol (2-5 ml) to yield 420 mg of trans-4,6,6a,8,9,10a-hexahydro-7-methyl-7H-indolo-[3,4 gh]-[1,4]-benzoxazine. This solid is purified by chromatography (silica, CHCl3 /NH4OH) to give 330 mg of trans-4,6,6a,8,9,10a-hexahydro-7-methyl-7-H-indolo-[3,4 gh]-[1,4]-benzoxazine; m.p. 175°-177° (softening at 100°).

Workup

  1. temperatureis refluxed for 17 hours
  2. filtrationThe solid is filtered
  3. dry with materialthe organic solvent is dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent is removed under reduced pressure (20 mm)
  6. customThe gum is crystallized from methanol (2-5 ml)

Sources & evidence

ORD record
ord-d3b2025baa714b03b368d7b68a821807
Source dataset
uspto-grants-1980_12
Patent number
US04238486

Reaction notes

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