Water → HCID 22813386, compound

HRID 1732586Notes

Reaction equation

HRID 1732586 reaction equation
[H-].[Na+].C1(C)C=CC(S([N:12]2[C:28]3[C:15]4=[C:16]([CH:25]=[CH:26][CH:27]=3)[C@H:17]3[O:22][CH2:21][C:20](=O)[NH:19][C@@H:18]3[CH2:24][C:14]4=[CH:13]2)(=O)=O)=CC=1.[CH3:30]I.O>CN(C=O)C>[CH3:30][N:19]1[C@@H:18]2[CH2:24][C:14]3[C:15]4[C:28]([NH:12][CH:13]=3)=[CH:27][CH:26]=[CH:25][C:16]=4[C@H:17]2[O:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54168596HCID 54168596, compound

Product 1

HCID 22813386HCID 22813386, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (50% in mineral oil, 1.1 gms, 0.045 m) is added in portions to a stirred solution of trans 4-(p-tolylsulphonyl)-4,6,6a,8,9,10a hexahydro-7H-indolo-[3,4 gh]-[1,4] benzoxazin-8-one (7.0 gm, 0.018 m) in DMF (14 ml). The resulting mixture is stirred at room temperature for 1/2 hour. Methyl iodide (5.0 gm, 0.035 m) is added dropwise to the reaction mixture. After stirring an additional 1/2 hour, the reaction solution is poured into water, and the solid is removed by filtration. The tan solid is chromatographed (silica, chloroform) to give 3 gms of trans-4,6,6a,8,9,10a-Hexahydro-7-methyl-7H-indolo-[3,4 gh]-[1.4]-benzoxazine.

Workup

  1. stirringAfter stirring an additional 1/2 hour
  2. customthe solid is removed by filtration
  3. customThe tan solid is chromatographed (silica, chloroform)

Sources & evidence

ORD record
ord-916b4392e01548c8a652d0363067e984
Source dataset
uspto-grants-1980_12
Patent number
US04238486

Reaction notes

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