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

HRID 2279910Notes

Reaction equation

HRID 2279910 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 89824027(S)-1-(3-[(tert-butyldimethylsilyl)oxy]butyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 67812823(2S)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-2-olYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-1-(3-[(tert-butyldimethylsilyl)oxy]butyl]-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 70C, 7.7 g, 20.2 mmol) in THF (30 mL) was treated with tetrabutylammonium fluoride (30 mL, 1M solution 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 (1 g, 20%). 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-1d9d46c17e61423e882cf3f466a41698
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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