Tetrabutylammonium Fluoride → HCID 89396982, compound

HRID 2171608Notes

Reaction equation

HRID 2171608 reaction equation
[Si]([O:8][C@@H:9]1[C@@H:16]2[N:12]([N:13]=[C:14]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[C:22]=3[CH3:30])[C@H:15]2[O:17][CH2:18][CH2:19][F:20])[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[Cl:29][C:23]1[C:22]([CH3:30])=[C:21]([C:14]2[C@@H:15]([O:17][CH2:18][CH2:19][F:20])[C@@H:16]3[C@@H:9]([OH:8])[CH2:10][CH2:11][N:12]3[N:13]=2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131732947HCID 131732947, compound

Product 1

HCID 89396982HCID 89396982, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-((3S,3aR,4S)-4-((tert-butyldimethylsilyl)oxy)-3-(2-fluoroethoxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile (30 mg, 0.0664 mmol) in THF (4 mL) at 0° C. was added TBAF (0.13 mL, 0.132 mmol, 1M Solution in THF) and stirred for 1 h at room temperature. Once the starting material had disappeared (monitored by TLC), reaction mixture was diluted with ethyl acetate. Organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Crude product was purified by preparative TLC method using 2% methanol in DCM as eluent.

Workup

  1. custom(monitored by TLC), reaction mixture
  2. washOrganic layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customCrude product was purified by preparative TLC method

Sources & evidence

ORD record
ord-b7b7526a0c88485dbefd22621eb9a7ac
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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