ethyl 3-[2-(N-tert-butyloxycarbonylamino)ethyl]-1H-indole-5-acetate → 3-[2-(N-Tert-butyloxycarbonylamino)ethyl]-5-(2-hydroxyethyl)-1H-indole

HRID 1613622Notes

Reaction equation

HRID 1613622 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][CH2:19][CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH2:30][C:31](OCC)=[O:32])[CH:28]=2)[NH:23][CH:22]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl.C(CC1C=CC(NN)=CC=1)(OCC)=O>>[C:11]([O:15][C:16]([NH:18][CH2:19][CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH2:30][CH2:31][OH:32])[CH:28]=2)[NH:23][CH:22]=1)=[O:17])([CH3:13])([CH3:14])[CH3:12]

Participants

4

Reactant 3

HCID 10450326ethyl 3-[2-(N-tert-butyloxycarbonylamino)ethyl]-1H-indole-5-acetateHCID 21225700DiisobutylaluminumhydrideHCID 21254104Ethyl (4-hydrazinophenyl)acetate hydrochloride

Product 1

HCID 99723123-[2-(N-Tert-butyloxycarbonylamino)ethyl]-5-(2-hydroxyethyl)-1H-indole

Procedure

Diisobutylaluminium hydride reduction of ethyl 3-[2-(N-tert-butyloxycarbonylamino)ethyl]-1H-indole-5-acetate using the conditions described for Intermediate 1 (Step 4) afforded the title compound as a colourless thick oil, after purification by flash chromatography (silica gel, diethyl ether); δH (250 MHz, CDCl3) 8.03 (1H, br s, indole N--H), 7.44 (1H, s, Ar--H), 7.32 (1H, d, J=8.3 Hz, Ar--H), 7.07 (1H, dd, J=8.3 and 1.6 Hz, Ar--H), 7.02 (1H, d, J=2.2 Hz, Ar--H), 4.60 (1H, br s, --NH--), 3.89 (2H, t, J=6.5 Hz, --CH2OH), 3.45 (2H, m, --CH2N--), 2.97 (2H, t, J=6.5 Hz, --CH2CH2OH), 2.93 (2H, t, J=6.8 Hz, --CH2 -- ), 1.43 (9H, s, t--Bu); m/z (CI) 303 (M+ -1). (Found: m/z 304.1759. C17H24N2O requires: m/z 304.1787).

Sources & evidence

ORD record
ord-80164c65d33642cabe324fe53dc8d686
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

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