64091-14-1 → HCID 68733852, compound

HRID 1470680Notes

Reaction equation

HRID 1470680 reaction equation
[Br-].[CH2:2]([PH3+])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CC(C)([O-])C.[K+].[Si:16]([O:23][C@@H:24]1[CH2:32][C@@H:27]2[O:28][C:29](=[O:31])[CH2:30][C@@H:26]2[C@H:25]1[CH:33]=O)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C1COCC1>[Si:16]([O:23][C@@H:24]1[CH2:32][C@@H:27]2[O:28][C:29](=[O:31])[CH2:30][C@@H:26]2[C@H:25]1[CH:33]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])([C:19]([CH3:20])([CH3:22])[CH3:21])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 1098974564091-14-1HCID 23665647Potassium tert-butoxideHCID 86630288HCID 86630288, compound

Product 1

HCID 68733852HCID 68733852, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-heptylphosphonium bromide (3.185 g, 7.22 mmol) was dried under vacuum for 3 days and was then taken into dry THF (22 mL). Potassium tert-butoxide (7.2 mL, 7.2 mmol, 1 M/THF) was added and the resulting red-orange solution was stirred for 45 min. at room temperature. A solution of (3aR,4R,5R,6aS)-5-(tert-butyldimethylsilyloxy)-2-oxohexahydro-2H-cyclopenta[b]furan-4-carbaldehyde (5-1, 502 mg, 1.78 mmol, Cayman) in 7 mL THF was added by cannula, rinsing with 3 mL THF. After 1.5 h, the reaction was quenched by addition of saturated NH4Cl solution. The resulting mixture was extracted with ethyl acetate (3×) and the combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (595 mg, 91%).

Workup

  1. washrinsing with 3 mL THF
  2. waitAfter 1.5 h
  3. customthe reaction was quenched by addition of saturated NH4Cl solution
  4. extractionThe resulting mixture was extracted with ethyl acetate (3×)
  5. dry with materialthe combined ethyl acetate solution was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification of the residue by flash chromatography on silica gel (Isco Combiflash unit)

Sources & evidence

ORD record
ord-2c611dcaa9524007ad009d5888c9284f
Source dataset
uspto-grants-2015_04
Patent number
US09006464B2

Reaction notes

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