N,N-Diethylethanamine trihydrofluoride → HCID 118161760, compound

HRID 2203670Notes

Reaction equation

HRID 2203670 reaction equation
[Si]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25]2[N:29]([CH:30]([CH3:32])[CH3:31])[N:28]=[C:27]([I:33])[CH:26]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.F.F.F.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[I:33][C:27]1[CH:26]=[C:25]([CH:22]2[CH:21]3[CH:23]2[CH2:24][CH:19]([OH:18])[CH2:20]3)[N:29]([CH:30]([CH3:32])[CH3:31])[N:28]=1

Participants

5

Reactant 3

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 516892Sodium BicarbonateHCID 123430411HCID 123430411, compound

Product 1

HCID 118161760HCID 118161760, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-3-iodo-1-isopropyl-1H-pyrazole (11.2 g, 19.7 mmol) and triethylamine trihydrofluoride (63 g, 391 mmol) in anhydrous tetrahydrofuran (100 mL) was heated at 70° C. for 6 h. Saturated aqueous sodium bicarbonate solution was added until the solution reached pH=7. The resulting aqueous mixture was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (5:1 petroleum either/ethyl acetate) afforded crude 6-(3-iodo-1-isopropyl-1H-pyrazol-5-yl)bicyclo[3.1.0]hexan-3-ol as a pale yellow oil (6.6 g, 100%). LRMS: [M+H]+ 332.9.

Workup

  1. extractionThe resulting aqueous mixture was extracted with ethyl acetate (2×100 mL)
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (5:1 petroleum either/ethyl acetate)

Sources & evidence

ORD record
ord-a627c4640d964233b658696a8af73fd8
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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