Acetic Acid → HCID 58742366, compound

HRID 1988093Notes

Reaction equation

HRID 1988093 reaction equation
[Si]([O:8][C:9]1[CH:22]=[C:21]2[C:12]([C@@:13]3([CH2:31][CH3:32])[C@H:18]([CH2:19][CH2:20]2)[CH2:17][C@:16]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)([OH:23])[C@@H:15]([OH:30])[CH2:14]3)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:31]([C@:13]12[C:12]3[C:21](=[CH:22][C:9]([OH:8])=[CH:10][CH:11]=3)[CH2:20][CH2:19][C@@H:18]1[CH2:17][C@:16]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)([OH:23])[C@@H:15]([OH:30])[CH2:14]2)[CH3:32]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 68832690HCID 68832690, compound

Product 1

HCID 58742366HCID 58742366, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2R,3S,4aR,10aR)-7-(tert-butyl-dimethylsilanyloxy)-4a-ethyl-2-(pyridin-3-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-2,3-diol (13 mg, 0.03 mmol) and acetic acid (0.05 mL, 0.87 mmol) in tetrahydrofuran (2 mL) was added a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.13 mL, 0.13 mmol). The mixture was stirred overnight at room temperature and the concentrated under vacuum. The residue was taken up in ethyl acetate and filtered through a plug of silica gel. The title compound, a solid (4.2 mg, 43%) was obtained by evaporation of the solvent. 1H NMR (CDCl3) selected signals: δ 9.00 (br s, 1H), 8.50 (d, J=8.3 Hz, 1H), 8.26 (d, J=5.7 Hz, 1H), 7.32 (dd, J=5.7, 7.8 Hz, 1H), 6.94 (d, J=8.3 Hz, 1H), 6.65 (dd, J=2.6, 8.3 Hz, 1H), 6.60 (d, J=2.6 Hz, 1H), 4.23 (dd, J=4.7, 13.0 Hz, 1H). MS: m/e 340 (M+1).

Workup

  1. concentrationthe concentrated under vacuum
  2. filtrationfiltered through a plug of silica gel

Sources & evidence

ORD record
ord-f8263c2198e44c3bb25a408fa66a0a53
Source dataset
uspto-grants-2009_06
Patent number
US07553877B2

Reaction notes

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