Water → 2-propanyl 4-[(3S,5aR,6R,7R,8aS)-6-[(1E)-4-phenoxy-1-buten-1-yl)-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

HRID 1915212Notes

Reaction equation

HRID 1915212 reaction equation
[CH3:1][Si](C)(C)N[Si](C)(C)C.[K].[C:11]1(C)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH:18]([C@@H:20]1[C@@H:29]2[C@@H:23]([O:24][CH2:25][C@@H:26]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:27][CH2:28]2)[CH2:22][C@H:21]1[O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1)=O.O.C([O:50][CH2:51][CH3:52])(=O)C>COCCOC>[O:50]([CH2:51][CH2:52]/[CH:1]=[CH:18]/[C@@H:20]1[C@@H:29]2[C@@H:23]([O:24][CH2:25][C@@H:26]([CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:27][CH2:28]2)[CH2:22][C@H:21]1[O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 866653202-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-formyl-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoateHCID 131731101HCID 131731101, compound

Product 1

HCID 687488212-propanyl 4-[(3S,5aR,6R,7R,8aS)-6-[(1E)-4-phenoxy-1-buten-1-yl)-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under the argon atmosphere, the compound (165 mg) produced in Example 100 was dissolved in DME (2 mL), the solution was cooled to −78° C., and a 0.5M potassium hexamethyldisilazane/toluene solution (0.90 mL) was added. After the mixture was stirred at −78° C. for 20 minutes, a DME (1.5 mL) solution of the compound produced in Example 13 was added dropwise, and the mixture was stirred at the same temperature for 10 minutes. After a temperature of the reaction solution was raised to 0° C., water was added, and the extract obtained by extraction with ethyl acetate was washed with water and a saturated saline, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→65:35) to obtain a titled compound (177 mg) having the following physical property values.

Workup

  1. stirringthe mixture was stirred at the same temperature for 10 minutes
  2. temperatureAfter a temperature of the reaction solution was raised to 0° C.
  3. washwas washed with water
  4. dry with materiala saturated saline, dried with anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→65:35)

Sources & evidence

ORD record
ord-ba267adc7f0149c5a750c7aaab63273b
Source dataset
uspto-grants-2013_12
Patent number
US08614340B2

Reaction notes

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