Tetrabutylammonium Fluoride → HCID 71239368, compound

HRID 2171609Notes

Reaction equation

HRID 2171609 reaction equation
[Si]([O:8][C@@H:9]1[C@@H:16]2[N:12]([N:13]=[C:14]([C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:30])[C:23]=3[CH3:31])[C@H:15]2[O:17][CH2:18][CH:19]2[CH2:21][CH2:20]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[Cl:30][C:24]1[C:23]([CH3:31])=[C:22]([C:14]2[C@@H:15]([O:17][CH2:18][CH:19]3[CH2:21][CH2:20]3)[C@@H:16]3[C@@H:9]([OH:8])[CH2:10][CH2:11][N:12]3[N:13]=2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131732948HCID 131732948, compound

Product 1

HCID 71239368HCID 71239368, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-((3S,3aR,4S)-4-((tert-butyldimethylsilyl)oxy)-3-(cyclopropylmethoxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile (60 mg, 0.13 mmol) in THF (2 mL) at 0° C. was added TBAF (0.26 mL, 0.26 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 (50% EtOAc in hexane).

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 (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-045359a429c945c7bc6f6c6dab6ac22b
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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