1-(2-cyclopropylethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one → 1-(2-cyclopropylethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one

HRID 545668Notes

Reaction equation

HRID 545668 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]([C:17]1[C:25]([OH:26])=[CH:24][C:20]3[O:21][CH2:22][O:23][C:19]=3[CH:18]=1)[C:5](=[O:16])[N:6]2[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C1(CCN2C3C(=CC=CC=3)C(C3C(O)=C[C:44]4[O:45]COC=4C=3)C2=O)CC1>>[CH:13]1([CH2:12][CH2:11][N:6]2[C:7]3[C:3](=[CH:2][CH:10]=[CH:9][CH:8]=3)[C:4]([C:17]3[C:25]([OH:26])=[CH:24][C:20]4[O:21][CH2:22][O:23][C:19]=4[CH:18]=3)([CH2:44][OH:45])[C:5]2=[O:16])[CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 120043801-(2-cyclopropylethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-oneHCID 588725004-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 666425671-(2-cyclopropylethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 1E, making variations to replace 4-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one with 1-(2-cyclopropylethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one, the title compound was obtained (53%): Rf=0.28 (EtOAc/Hexanes, 1/1).

Sources & evidence

ORD record
ord-8375f35dea514916b4e70010c7318d17
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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