Tetrabutylammonium Fluoride → HCID 66732283, compound

HRID 1963123Notes

Reaction equation

[Si]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH:12]([CH2:20][C:21]([CH3:29])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])[CH2:11]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[OH:8][CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH:12]([CH2:20][C:21]([CH3:29])([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:22])[CH2:11]1

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 66732327HCID 66732327, compound

Product 1

HCID 66732283HCID 66732283, compound

Procedure

The compound was prepared as described in Reference Compound 4, Step 4 starting from crude methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-(2-methyl-2-phenylpropyl)piperidine-1-carboxylate (16.5 g) and TBAF (46.5 mL, 46.6 mmol, 1 M in THF). The residue was purified by column chromatography (Biotage 40-65% gradient EtOAc in heptane, 340 snap column, 2 runs), which resulted in the titled compound. MS m/z 306 (M+H)+.

Workup

customThe compound was prepared
customThe residue was purified by column chromatography (Biotage 40-65% gradient EtOAc in heptane, 340 snap column, 2 runs), which

Sources & evidence

ORD record: ord-8b0dae4862a24abda18f146bda47dd5a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415378B2

Reaction notes

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