Tetrabutylammonium Fluoride → HCID 118377801, compound

HRID 1055499Notes

Reaction equation

HRID 1055499 reaction equation
C([Si](C)(C)[O:6][CH2:7][C@@H:8]1[C@@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@H:12]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:11]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@:10]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[C:42]([CH2:47][C:48]3[CH:53]=[CH:52][C:51]([O:54][CH2:55][CH3:56])=[CH:50][CH:49]=3)[CH:41]=2)([O:38][CH3:39])[O:9]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:15]([O:14][C@H:13]1[C@H:12]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@@H:11]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@:10]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[C:42]([CH2:47][C:48]3[CH:49]=[CH:50][C:51]([O:54][CH2:55][CH3:56])=[CH:52][CH:53]=3)[CH:41]=2)([O:38][CH3:39])[O:9][C@@H:8]1[CH2:7][OH:6])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131736379HCID 131736379, compound

Product 1

HCID 118377801HCID 118377801, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl-dimethyl-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methoxy-tetrahydropyran-2-yl]methoxy]silane 1f (84.1 g, 102.1 mmol) in tetrahydrofuran (400 mL) was added tetrabutylammonium fluoride (53.4 g, 204.2 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours and quenched with 100 mL of saturated aqueous sodium bicarbonate. The resulting mixture was washed with water (100 mL). The aqueous layer was extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with saturated aqueous sodium chloride (200 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 1g as yellow oil (56.3 g, 77.8%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ (ppm): 7.34 (m, 13H), 7.25 (m, 3H), 7.04 (m, 2H), 6.99 (m, 2H), 6.77 (m, 2H), 4.90 (m, 3H), 4.69 (d, 1H), 4.49 (d, 1H), 4.16 (t, 1H), 4.10 (d, 1H), 4.00 (m, 2H), 3.98 (m, 2H), 3.81 (m, 1H), 3.70 (m, 1H), 3.68 (m, 1H), 3.66 (m, 1H), 3.29 (d, 1H), 3.06 (s, 3H), 1.75 (bs, 1H), 1.38 (t, 3H).

Workup

  1. customquenched with 100 mL of saturated aqueous sodium bicarbonate
  2. washThe resulting mixture was washed with water (100 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (100 mL×3)
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with PE/EtOAc(v/v)=10/1

Sources & evidence

ORD record
ord-f4cf64781d184311807adc4a10e3ab69
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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