Tetrabutylammonium Fluoride → (2R)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-ol

HRID 2279908Notes

Reaction equation

HRID 2279908 reaction equation
[Si]([O:8][C@H:9]([CH3:26])[CH2:10][CH2:11][N:12]1[CH:16]=[C:15]([B:17]2[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]2)[CH:14]=[N:13]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:25][C:19]1([CH3:24])[C:20]([CH3:22])([CH3:23])[O:21][B:17]([C:15]2[CH:14]=[N:13][N:12]([CH2:11][CH2:10][C@H:9]([OH:8])[CH3:26])[CH:16]=2)[O:18]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67817517(R)-1-(3-[(tert-butyldimethylsilyl)oxy]butyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 67817524(2R)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-olYield 17.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-1-(3-[(tert-butyldimethylsilyl)oxy]butyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 69C, 5 g, 13.1 mmol) in THF (20 mL) was treated with tetrabutylammonium fluoride (26 mL, 1M in THF) and stirred for 24 hrs at RT under nitrogen atmosphere. Tetrahydrofuran was evaporated under reduced pressure and the residue was purified by column chromatography (SiO2, 1% methanol in dichloromethane) to give colorless gum (600 mg, 17%). 1H NMR (400 MHz, CDCl3) δ 7.74 (s, 1H), 7.64 (s, 1H), 4.15-4.23 (m, 2H), 3.60-3.3.71 (m, 1H), 1.7-1.98 (m, 2H), 1.23 (s, 12H), 1.12 (s, d, 3H).

Workup

  1. customTetrahydrofuran was evaporated under reduced pressure
  2. customthe residue was purified by column chromatography (SiO2, 1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-856f3f30619f431bb757677991261f50
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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