tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate → tert-Butyl 4-(hydroxymethyl)-1H-indole-1-carboxylate

HRID 551509Notes

Reaction equation

HRID 551509 reaction equation
C(OC(N1C2C(=CC=C(CO)C=2)C=C1)=O)(C)(C)C.[C:19]([O:23][C:24]([N:26]1[C:34]2[C:29](=[C:30]([CH:35]=[O:36])[CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24]([N:26]1[C:34]2[C:29](=[C:30]([CH2:35][OH:36])[CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

3

Reactant 2

HCID 23560816tert-Butyl 6-(hydroxymethyl)-1H-indole-1-carboxylateHCID 49758854Tert-butyl 4-formyl-1H-indole-1-carboxylate

Product 1

HCID 12148524tert-Butyl 4-(hydroxymethyl)-1H-indole-1-carboxylate

Procedure

4-Hydroxymethyl-indole-1-carboxylic acid tert-butyl ester was synthesized by a procedure similar to 6-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester from starting material 4-formyl-indole-1-carboxylic acid tert-butyl ester to yield the product as a clear viscous oil (0.91 g, 78%). LC-MS (ES) calculated for C14H17NO3, 247.1; found m/z 246 [M+H]+.

Sources & evidence

ORD record
ord-1c26ff9dcb044f2c8c07742fcab35fd5
Source dataset
uspto-grants-2011_05
Patent number
US07947728B1

Reaction notes

Loading…