Sodium Hydroxide → HCID 12946388, compound

HRID 1380628Notes

Reaction equation

HRID 1380628 reaction equation
[Br:1][CH:2]1[CH2:10][CH2:9][C:8]2[N:7]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:5][C:4]=2[C:3]1=[O:21].[CH2:22]([CH:24]1[O:26][CH2:25]1)[Br:23].[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH:2]1[C:3]2([O:26][CH:24]([CH2:22][Br:23])[CH2:25][O:21]2)[C:4]2[CH:5]=[CH:6][N:7]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:8]=2[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18430EpibromohydrinHCID 129463865-Bromo-1-(4-methylbenzene-1-sulfonyl)-1,5,6,7-tetrahydro-4H-indol-4-one

Product 1

HCID 12946388HCID 12946388, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 5-bromo-1-p-toluenesulfonyl-4-oxo-4,5,6,7-tetrahydroindole (100 parts), epibromohydrin (1.2 molar equivalents) and stannic chloride (0.1 molar equivalent in carbon tetrachloride (1500 parts) is kept at 0° C. to 2° C. for 19 hours. The reaction mixture is carefully mixed with 5N-sodium hydroxide to adjust at pH 10, shaken and organic layer separated. By washing with water, drying and concentration, the organic layer gives 72.3% yield of 5-bromo-4'-bromomethyl-1-p-toluenesulfonyl-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]dioxolane diastereomer mixture. Amounts show ratios to the starting 5-bromo-1-p-toluenesulfonyl-4,5,6,7-tetrahydroindol-4-one.

Workup

  1. customorganic layer separated
  2. washBy washing with water
  3. customdrying
  4. concentrationconcentration

Sources & evidence

ORD record
ord-55992564db9c41edbee5bbcd382a0b45
Source dataset
uspto-grants-1986_04
Patent number
US04582905

Reaction notes

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