Tetrabutylammonium Fluoride → HCID 86623610, compound

HRID 1431986Notes

Reaction equation

HRID 1431986 reaction equation
[Si]([O:8][C@@H:9]1[C:18]2[C:13](=[CH:14][C:15](CN3CCC(F)CC3)=[CH:16][CH:17]=2)[O:12][CH2:11][CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+:31]([CH2:40][CH2:41][CH2:42][CH3:43])([CH2:36]CCC)[CH2:32]CCC.[F-:44]>C1COCC1.O>[F:44][CH:42]1[CH2:43][CH2:36][N:31]([CH2:32][CH:11]2[CH2:10][CH:9]([OH:8])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[O:12]2)[CH2:40][CH2:41]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59771817HCID 59771817, compound

Product 1

HCID 86623610HCID 86623610, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (5)-1-((4-(tert-butyldimethylsilyloxy)-3,4-dihydro-2H-chromen-7-yl)methyl)-4-fluoropiperidine (4.54 g, 12.5 mmol) and TBAF (7.92 g, 37.49 mmol) in THF (50 mL) was stirred for 16 h at RT. The reaction mixture was taken up in H2O, and extracted with EtOAc (3×). The organic layers were extracted with 10% aqueous HCl. The combined aqueous extracts were neutralized with 2N NaOH, and extracted with CH2Cl2 (3×). The combined organic extracts were dried over MgSO4 and concentrated to give the title compound as a yellow oil. MS (m/z, m+1): 282.4.

Workup

  1. extractionextracted with EtOAc (3×)
  2. extractionThe organic layers were extracted with 10% aqueous HCl
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9cfb4b5e3aaa4675a9a5776b32419678
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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