Tetrabutylammonium Fluoride → HCID 54338219, compound

HRID 1939835Notes

Reaction equation

HRID 1939835 reaction equation
[CH3:1][O:2][N:3]=[C:4]([CH:14]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][C:20]([OH:29])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)[CH2:5][O:6][Si](C)(C)C(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][O:2][N:3]=[C:4]([CH:14]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][C:20]([OH:29])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54123312HCID 54123312, compound

Product 1

HCID 54338219HCID 54338219, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of the crude oxime from Step 3 (≤12.3 mmol) in THF (400 mL) with TBAF (15.4 mL, 15.4 mmol, 1M in THF) at 0° C. Stir the solution for 2 hours. Quench the reaction with water and extract the aqueous phase with EtOAc (3×100 mL). Dry the combined organic layers over MgSO4, filter and concentrate under reduced pressure to give the crude product as a yellow oil. Purify by silica gel chromatography (column: 7.5 cm×20 cm; pack column in CH2Cl2 and elute using a gradient of 100% CH2Cl2 to 5% CH3 OH(NH3)/CH2Cl2) to obtain 16 g (29.9 mmol, 75% from Example CAA2) of the title compound as a white solid. HRMS (FAB, M+H+): m/e cal'd for [C23H29N2O3Cl2 ]+ : 451.1555, found 451.1553 .

Workup

  1. customQuench
  2. customthe reaction with water
  3. extractionextract the aqueous phase with EtOAc (3×100 mL)
  4. dry with materialDry the combined organic layers over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give the crude product as a yellow oil
  8. customPurify by silica gel chromatography (column
  9. washpack column in CH2Cl2 and elute

Sources & evidence

ORD record
ord-25aeaa5f8efc4465b3015481e8e32633
Source dataset
uspto-grants-1997_12
Patent number
US05696267

Reaction notes

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