HCID 131733348, compound → HCID 117891129, compound

HRID 517400Notes

Reaction equation

HRID 517400 reaction equation
[Si]([O:8][CH:9]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:10][CH2:11][C@@H:12]1[C@@H:24]2[C@@H:15]([O:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23]2)[CH2:14][C@H:13]1[O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)(C(C)(C)C)(C)C>O1CCCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[OH:8][CH:9]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:10][CH2:11][C@@H:12]1[C@@H:24]2[C@@H:15]([O:16][C:17](=[O:25])[CH2:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23]2)[CH2:14][C@H:13]1[O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1

Participants

4

Reactant 1

HCID 131733348HCID 131733348, compound

Product 1

HCID 117891129HCID 117891129, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of (8aR,9R,10R,11aS,Z)-9-[3-(tert-butyldimethylsilyloxy)decyl)-10-(tetrahydro-2H-pyran-2-yloxy)-4,5,8,8a,9,10,11,11a-octahydrocyclo-penta[b]oxecin-2(3H)-one (25 g, 44 mmol) in 350 ml tetrahydrofuran and 49 ml TBAF (1M in tetrahydrofuran) were added into 1-liter round-bottom flask. The reaction mixture was stirred at 50° C. for 3 hours and quenched by 200 ml saturated NaHCO3 aqueous solution. Then, the mixture was phase separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous MgSO4. The solid was filtered off and organic solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield of the titled compound was 15 g (75%).

Workup

  1. customquenched by 200 ml saturated NaHCO3 aqueous solution
  2. customseparated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationThe solid was filtered off
  6. customorganic solvent was evaporated off under vacuum
  7. customThe crude product was purified by chromatography on silica gel using
  8. additiona mixture of hexane and ethyl acetate as a gradient eluent

Sources & evidence

ORD record
ord-ca5dd03fefb94ff69e45d4644462afa1
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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