methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylate → 1-Methylindolin-2-ylmethanol

HRID 1953672Notes

Reaction equation

HRID 1953672 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[C:11](OC)=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 12658762methyl 1-methyl-2,3-dihydro-1H-indole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 232982881-Methylindolin-2-ylmethanolYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Preparation 2 was repeated, except that 8.0 g of methyl 1-methyl-indoline-2-carboxylate (prepared as described in Preparation 5), 1.91 g of lithium aluminum hydride and 250 ml of tetrahydrofuran were used, to give 6.85 g of the title compound having Rf=0.35 (on silica gel thin layer chromatography using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 2

Sources & evidence

ORD record
ord-34ec18ff90a344e79dd28cda12f26948
Source dataset
uspto-grants-2000_09
Patent number
US06117893

Reaction notes

Loading…