Tetrabutylammonium Fluoride → HCID 58456720, compound

HRID 2036139Notes

Reaction equation

HRID 2036139 reaction equation
[Si]([O:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([C:16]2([OH:29])[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:11][C:10]=1[F:30])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:30][C:10]1[CH:11]=[C:12]([C:16]2([OH:29])[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:18][CH2:17]2)[CH:13]=[C:14]([F:15])[C:9]=1[OH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58456690HCID 58456690, compound

Product 1

HCID 58456720HCID 58456720, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl 4-(4-((tert-butyldimethylsilyl)oxy)-3,5-difluorophenyl)-4-hydroxypiperidine-1-carboxylate D1e (1.0 g, 2.25 mmol) in tetrahydrofurane (10 mL) is treated with a solution of tetra-n-butylammonium fluoride in tetrahydrofurane (1.0 M; 3 mL, 1.33 mmol). The mixture is stirred at room temperature for 4 hours. Concentration and purification by flash chromatography (hexanes/ethyl acetate gradient) affords tert-butyl 4-(3,5-difluoro-4-hydroxyphenyl)-4-hydroxypiperidine-1-carboxylate D1f as an oil. 1H-NMR (400 MHz, CDCl3) δ=7.01 (d, J=7.2 Hz, 2H), 4.03 (br. s, 2H), 3.19 (br. t, J=11 Hz, 2H), 1.89 (br. t, J=11 Hz, 2H), 1.67 (d, J=12.5 Hz, 2H), 1.58 (s, 1H), 1.48 (s, 9H); 19F-NMR (376 MHz, CDCl3) δ=−134.41. No MS spectrum could be obtained.

Workup

  1. concentrationConcentration and purification by flash chromatography (hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-228a073fd54d4cbf93925ece98034d6f
Source dataset
uspto-grants-2013_11
Patent number
US08575168B2

Reaction notes

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