Tetrabutylammonium Fluoride → tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(3-methoxypropyl)-1H-benzoimidazol-4-ylmethoxy]piperidine-1-carboxylate

HRID 1712538Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:57]=[CH:56][CH:55]=[CH:54][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][C:32]2[C:40]3[N:39]=[C:38]([CH2:41][CH2:42][CH2:43][O:44][CH3:45])[N:37](COCC[Si](C)(C)C)[C:36]=3[CH:35]=[CH:34][CH:33]=2)=[CH:13][CH:12]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH3:1][O:2][C:3]1[CH:57]=[CH:56][CH:55]=[CH:54][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][C:32]2[C:40]3[N:39]=[C:38]([CH2:41][CH2:42][CH2:43][O:44][CH3:45])[NH:37][C:36]=3[CH:35]=[CH:34][CH:33]=2)=[CH:13][CH:12]=1

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 68499525tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(3-methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazol-4-ylmethoxy]piperidine-1-carboxylate

Product 1

HCID 68502280tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(3-methoxypropyl)-1H-benzoimidazol-4-ylmethoxy]piperidine-1-carboxylate

Procedure

Analogously to Example 228a, 0.5 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-[2-(3-methoxypropyl)-1-(2-trimethylsilanylethoxymethyl)-1H-benzoimidazol-4-ylmethoxy]piperidine-1-carboxylate and 5.44 ml of tetrabutylammonium fluoride solution (1M in tetrahydrofuran) are reacted. The title compound is obtained as a yellowish oil. Rf=0.40 (1:1 EtOAc-heptane); Rt=4.99.

Sources & evidence

ORD record: ord-e35ec052408344cd9c885b38665d2235
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790715B2

Reaction notes

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