Hydrochloric Acid → HCID 86739992, compound

HRID 2164664Notes

Reaction equation

HRID 2164664 reaction equation
[CH2-]C(C)=O.[C:5]1([CH3:20])[CH:10]=[CH:9][C:8]([S:11]([O:14][CH2:15][CH:16]([OH:19])CO)(=[O:13])=[O:12])=[CH:7][CH:6]=1.[Br:21][CH:22]1[CH2:30][CH2:29][C:28]2[N:27]([S:31]([C:34]3[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[CH:26]=[CH:25][C:24]=2[C:23]1=[O:41].Cl.[OH-].[Na+]>O.C1C=CC=CC=1>[C:5]1([CH3:20])[CH:6]=[CH:7][C:8]([S:11]([O:14][CH:15]2[CH2:16][O:19][C:23]3([CH:22]([Br:21])[CH2:30][CH2:29][C:28]4[N:27]([S:31]([C:34]5[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=5)(=[O:33])=[O:32])[CH:26]=[CH:25][C:24]3=4)[O:41]2)(=[O:12])=[O:13])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 129463865-Bromo-1-(4-methylbenzene-1-sulfonyl)-1,5,6,7-tetrahydro-4H-indol-4-oneHCID 178427781HCID 178427781, compound

Product 1

HCID 86739992HCID 86739992, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 3-p-toluenesulfonyloxypropyleneglycol acetonide (2 molar equivalents), 5-bromo-1-p-toluenesulfonyl-4-oxo-4,5,6,7-tetrahydroindole (100 parts), hydrochloric acid (1 molar equivalent) and benzene (500 to 2000 parts) is refluxed for 21 hours under azeotropic dehydration. After cooling, the reaction mixture is adjusted to pH 10 with 5N-sodium hydroxide, shaken and water layer drained. Organic layer is washed with water, (100 parts) and dried over anhydrous sodium sulfate (50 parts). The drying agent is removed by filtration. The filtrate is then concentrated under reduced pressure at a temperature below 50° C. to leave amorphous 4'-p-toluenesulfonyloxy-1-p-toluenesulfonyl-5-bromo-4,5,6,7-tetrahydroindole-4-spiro-2'-[1,3]-dioxolane diastereomer mixture in 42% yield. The product is shown in Table I, Part 6, No. 18.

Workup

  1. temperatureis refluxed for 21 hours under azeotropic dehydration
  2. temperatureAfter cooling
  3. washOrganic layer is washed with water, (100 parts)
  4. dry with materialdried over anhydrous sodium sulfate (50 parts)
  5. customThe drying agent is removed by filtration
  6. concentrationThe filtrate is then concentrated under reduced pressure at a temperature below 50° C.

Sources & evidence

ORD record
ord-69976aea8fd041daae81bd7dcc4809c9
Source dataset
uspto-grants-1985_03
Patent number
US04506079

Reaction notes

Loading…