Tetrabutylammonium Fluoride → HCID 66732003, compound

HRID 1963121Notes

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]([CH3:20])[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]([CH3:20])[CH2:11]1

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

HCID 66732037HCID 66732037, compound

Product 1

HCID 66732003HCID 66732003, compound

Procedure

The compound was prepared as described in Reference Compound 4, Step 4 starting from methyl 4-((tert-butyldimethylsilyloxy)methyl)-2-methylpiperidine-1-carboxylate and TBAF (10.65 mL, 10.65 mmol, 1 M in THF). The residue was purified by column chromatography (Biotage 40%-90% gradient EtOAc in heptane, 340 snap column), which resulted in the title compound. 1H NMR (400 MHz, cdcl3) δ 0.95-1.42 (m, 3H), 1.68-1.95 (m, 3H), 3.08 (m, 1H), 3.39-3.53 (m, 2H), 3.61 (m, 1H), 3.68 (s, 3H), 3.71-3.87 (m, 1H), 3.87-4.08 (m, 1H), 4.30-4.62 (m, 1H).

Workup

customThe compound was prepared
customThe residue was purified by column chromatography (Biotage 40%-90% gradient EtOAc in heptane, 340 snap column), which

Sources & evidence

ORD record: ord-a57e84778faa4b0ba2ef7c95fa90fd72
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415378B2

Reaction notes

Loading…