Cyclohexanol → 1h-Indole-1-carboxylic acid,5-[(cyclohexyloxy)methyl]-,1,1-dimethylethyl ester

HRID 2249906Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17]Cl)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:19]1([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>C(OCC)C>[C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][O:25][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of 5-chloromethyl-indole-1-carboxylic acid tert-butyl ester (0.41 g, 1.55 mmol, 1.0 eq.), cyclohexanol (0.82 mL, 5.0 eq.) and Ag2O (1.80 g, 5.0 eq.) in diethyl ether (5 mL) was stirred at 35° C. over weekend. After cooling to room temperature, the reaction mixture was filtered through celite washing with ether. The filtrate was concentrated and the residue was purified by chromatography (3% EtOAc/hexanes) to give N-Boc-5-cyclohexyloxymethylindole (160 mg, 28%) as colorless oil. 1HNMR comfirmed the compound.

Workup

temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered
washthrough celite washing with ether
concentrationThe filtrate was concentrated
customthe residue was purified by chromatography (3% EtOAc/hexanes)

Sources & evidence

ORD record: ord-2653dddde2504b6db8f9547d751ba85e
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07314936B2

Reaction notes

Loading…