Tetrabutylammonium Fluoride → HCID 10184545, compound

HRID 1005078Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH2:19][O:20][CH:21]2[CH:26]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH:25]([CH2:34][CH2:35][CH3:36])[CH2:24][N:23](C(OCC[Si](C)(C)C)=O)[CH2:22]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH2:19][O:20][CH:21]2[CH:26]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)[CH:25]([CH2:34][CH2:35][CH3:36])[CH2:24][NH:23][CH2:22]2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 86604430HCID 86604430, compound

Product 1

HCID 10184545HCID 10184545, compound

Procedure

In an analogous manner to that described in Example 5, by treating 2-trimethylsilanylethyl (3RS,4RS, 5SR)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(4-fluoro-phenyl)-5-propyl-piperidine-1-carboxylate with tetrabutylammonium fluoride solution there was obtained (3RS,4RS,5SR)-3-(4-benzyloxy-naphthalen-2-ylmethoxy)-4-(4-fluoro-phenyl)-5-propyl-piperidine as an almost colourless solid, MS: 484 (M+H)+.

Sources & evidence

ORD record: ord-30e471961e434a7f8809792ffa585a25
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06051712

Reaction notes

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