Benzyl Bromide → 2-(2-Benzyloxyethyl)-3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane

HRID 37060Notes

Reaction equation

HRID 37060 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([C:25](=[O:49])[NH:26][CH2:27][CH2:28][NH:29][C:30]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:5][C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[Na+].[CH2:52](Br)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH2:52]([O:1][CH2:2][CH2:3][CH:4]([C:25](=[O:49])[NH:26][CH2:27][CH2:28][NH:29][C:30]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[NH:5][C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 194385132-(2-Hydroxyethyl)3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane

Product 1

HCID 194385562-(2-Benzyloxyethyl)-3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Hydroxyethyl)-3-oxo-1,7-bis(triphenylmethyl)-1,4,7-triazaheptane (10 mmol) is reacted as described by S. Czernecki et al. Tetr. Lett. (1976) 3535 with 80% sodium hydride (11 mmol) and benzylbromide (10 mmol) catalysed by tetrabutyl ammonium iodide (1 mmol) for 24 hours at ambient temperature (in 100 ml dry THF). 2-(2-Benzyloxyethyl)-3-oxo-1,7-bis(triphenylmethyl) -1,4,7-triazaheptane is purified by chromatography on silica.

Workup

  1. custom2-(2-Benzyloxyethyl)-3-oxo-1,7-bis(triphenylmethyl) -1,4,7-triazaheptane is purified by chromatography on silica

Sources & evidence

ORD record
ord-462456e371b24950b0f7d2025fe5ce07
Source dataset
uspto-grants-1995_05
Patent number
US05419893

Reaction notes

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