Tetrabutylammonium Fluoride → HCID 20795048, compound

HRID 1070589Notes

Reaction equation

HRID 1070589 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, 1M 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-b04bba846df64ea097bd34e3910fcf67
Source dataset
uspto-grants-2005_06
Patent number
US06903110B2

Reaction notes

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