Tetrabutylammonium Fluoride → HCID 20795048, compound

HRID 1796712Notes

Reaction equation

HRID 1796712 reaction equation
C([SiH2][O:6][C:7](C)(C)[C@H:8]1[CH2:21][CH2:20][C:19]2[C:10](=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][CH:13]=[CH:12]3)[O:9]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[N:15]1[C:16]2[C:11](=[C:10]3[C:19](=[CH:18][CH:17]=2)[CH2:20][CH2:21][C@H:8]([CH2:7][OH:6])[O:9]3)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131724983HCID 131724983, compound

Product 1

HCID 20795048HCID 20795048, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (6R)-6-(tert-butyl-dimethyl-silanyloxymethyl)-7,8-dihydro-6H-5-oxa-1-aza-phenanthrene (0.60 g, 1.82 mmole) in tetrahydrofuran (50 mL) was added tetra-n-butylammonium fluoride (2 mL, 1 M in THF). The reaction mixture was stirred for 20 minutes, then diluted with ethyl acetate and washed with water, dried over sodium sulfate, and the solvent removed in vacuum. The residue was purified by column chromatography on silica gel (50% methylene chloride/hexane) to afford 0.38 g (98%) of the title compound as a white solid, mp 128° C., [α]25D=+113.81° (c=5.9, CHCl3).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customthe solvent removed in vacuum
  4. customThe residue was purified by column chromatography on silica gel (50% methylene chloride/hexane)

Sources & evidence

ORD record
ord-bc45318dfe594043b32c5a5d47b660c8
Source dataset
uspto-grants-2006_04
Patent number
US07030245B2

Reaction notes

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