Hydrochloric Acid → 4-[2-(9-Benzenesulfonyl-1,3,4,9-tetrahydro-beta-carbolin-2-yl)-1-hydroxyethyl]cyclohexanone

HRID 2063731Notes

Reaction equation

HRID 2063731 reaction equation
Cl.[C:2]1([S:8]([N:11]2[C:23]3[CH2:22][N:21]([CH2:24][CH:25]([CH:27]4[CH2:36][CH2:35][C:30]5(OCC[O:31]5)[CH2:29][CH2:28]4)[OH:26])[CH2:20][CH2:19][C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[C:2]1([S:8]([N:11]2[C:23]3[CH2:22][N:21]([CH2:24][CH:25]([CH:27]4[CH2:28][CH2:29][C:30](=[O:31])[CH2:35][CH2:36]4)[OH:26])[CH2:20][CH2:19][C:18]=3[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)(=[O:10])=[O:9])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 698120402-(9-Benzenesulfonyl-1,3,4,9-tetrahydro-beta-carbolin-2-yl)-1-(1,4-dioxaspiro[4.5]dec-8-yl)ethanol

Product 1

HCID 698122624-[2-(9-Benzenesulfonyl-1,3,4,9-tetrahydro-beta-carbolin-2-yl)-1-hydroxyethyl]cyclohexanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 M hydrochloric acid (30 ml) was added to a solution of the product from stage 4 (748 mg, 1.50 mmol) in tetrahydrofuran (30 ml) and the mixture was stirred at room temperature for 16 h. The mixture was rendered alkaline with 4 M sodium hydroxide solution and extracted with ethyl acetate (3×35 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac.

Workup

  1. extractionextracted with ethyl acetate (3×35 ml)
  2. dry with materialThe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated i

Sources & evidence

ORD record
ord-7b85cb26bb064eff8bb05b0c61eead5a
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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