3,4-Dimethylphenol → 3-hydroxy-3-(7-hydroxy-4H-1,3-benzodioxin-6-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one

HRID 1407438Notes

Reaction equation

HRID 1407438 reaction equation
[O:1]1[C:6]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=2[CH2:4][O:3][CH2:2]1.CC1C=C(O)C=CC=1C.[O:21]1[CH2:25][CH2:24][CH2:23][C@@H:22]1[CH2:26][N:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:36])[C:28]1=[O:37].C1(C(C2C=CC=CC=2)N2C3C(=CC=CC=3)C(=O)C2=O)C=CC=CC=1>>[OH:36][C:29]1([C:9]2[C:8]([OH:11])=[CH:7][C:6]3[O:1][CH2:2][O:3][CH2:4][C:5]=3[CH:10]=2)[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:27]([CH2:26][C@H:22]2[CH2:23][CH2:24][CH2:25][O:21]2)[C:28]1=[O:37]

Participants

5

Reactant 4

HCID 72493,4-DimethylphenolHCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 67358326(R)-1-((tetrahydrofuran-2-yl)methyl)indoline-2,3-dioneHCID 685994544H-benzo[d][1,3]dioxin-7-ol

Product 1

HCID 686011473-hydroxy-3-(7-hydroxy-4H-1,3-benzodioxin-6-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 6A, and making non-critical variations using 4H-benzo[d][1,3]dioxin-7-ol to replace 3,4-dimethylphenol, and (R)-1-((tetrahydrofuran-2-yl)methyl)indoline-2,3-dione to replace 1-(diphenylmethyl)-1H-indole-2,3-dione, 3-hydroxy-3-(7-hydroxy-4H-1,3-benzodioxin-6-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one was obtained (62%) as a colorless solid: MS (ES+) m/z 366.2 (M−17).

Sources & evidence

ORD record
ord-3aca7977026e44a2b9bbd8de3d947bbe
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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