Indoline-4-ol → tert-Butyl 5-((4-hydroxyindolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710392Notes

Reaction equation

HRID 710392 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2.OC1C=C2C(=CC=1)N([CH2:21][C:22]1([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:27][O:26][C:25]([CH3:29])([CH3:28])[O:24][CH2:23]1)CC2>>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][N:6]2[CH2:21][C:22]1([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:27][O:26][C:25]([CH3:28])([CH3:29])[O:24][CH2:23]1

Participants

3

Reactant 2

HCID 3021054Indoline-4-olHCID 66726286tert-Butyl 5-((5-hydroxyindolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 86661791tert-Butyl 5-((4-hydroxyindolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 74%

Procedure

When the product of Step A was substituted for tert-butyl 5-((5-hydroxyindolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate in Example 8, Step G, the identical process afforded the title compound in 74% yield, as a creamy solid. 1H-NMR (CDCl3) 1.4-1.65 (m, 15H+H2O); 2.94 (tr, 2H, J=8.4 Hz); 3.5 (tr, 2H, J=8.4 Hz); 3.52 (s, 2H); 3.8-3.99 (m, 4H); 4.64 (broad s, 1H); 4.7 (broad s, 1H); 6.15-6.23 (m, 2H); 6.93 (tr, 1H, J=7.96 Hz).

Sources & evidence

ORD record
ord-cd14a5a0b46744c7b3883dc5d350bcbc
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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