Ethyl Acetate → 3-{1-(1,3-Benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonamido]-2-oxoethyl}-6-(hydroxymethyl)-1-methyl-1h-indole

HRID 1934615Notes

Reaction equation

HRID 1934615 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]([C:32]3[C:40]4[C:35](=[CH:36][C:37]([C:41](OC)=[O:42])=[CH:38][CH:39]=4)[N:34]([CH3:45])[CH:33]=3)[C:17]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=3[O:30][CH3:31])(=[O:22])=[O:21])=[O:18])=[CH:15][C:10]=2[O:9][CH2:8]1.C(OCC)(=O)C>O1CCCC1>[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]([C:32]3[C:40]4[C:35](=[CH:36][C:37]([CH2:41][OH:42])=[CH:38][CH:39]=4)[N:34]([CH3:45])[CH:33]=3)[C:17]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=3[O:30][CH3:31])(=[O:22])=[O:21])=[O:18])=[CH:15][C:10]=2[O:9][CH2:8]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 224672003-{1-(1,3-Benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonamido]-2-oxoethyl}-6-(methoxycarbonyl)-1-methyl-1h-indole

Product 1

HCID 224672663-{1-(1,3-Benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonamido]-2-oxoethyl}-6-(hydroxymethyl)-1-methyl-1h-indoleYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (15 mg, 0.2 mmol) was added slowly to a stirred solution of methyl 3-{1-(1,3-benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-6-indolecarboxylate (from step (a), 220 mg, 0.4 mmol) in tetrahydrofuran at 0° C. under a nitrogen atmosphere. After 2 h a further 1 equivalent (30 mg) of lithium aluminium hydride was added and the mixture was warmed to room temperature. After 1 h ethyl acetate (10 ml) was carefully added and the product extracted from 1N hydrochloric acid with ethyl acetate (2×50 ml). The combined organic layers were dried (MgSO4) and concentrated in vacuo. Purification by flash column chromatography (elution with 95% dichloromethane/5% methanol) gave the product as a white solid (130 mg).

Workup

  1. extractionthe product extracted from 1N hydrochloric acid with ethyl acetate (2×50 ml)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification
  5. washby flash column chromatography (elution with 95% dichloromethane/5% methanol)

Sources & evidence

ORD record
ord-61bf3688480547d59fcde0547d2aa47c
Source dataset
uspto-grants-2002_05
Patent number
US06384070B2

Reaction notes

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