HCID 11797378, compound → HCID 10764915, compound

HRID 1078497Notes

Reaction equation

HRID 1078497 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[CH:26]=[C:25]([C:30]([O:32][CH3:33])=[O:31])[CH:24]=[CH:23]5)[CH:14]=[CH:15][C:16]=3[C:17](O)=[O:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2>C1COCC1>[C:1]12([C:11]3[CH:12]=[C:13]([C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[CH:26]=[C:25]([C:30]([O:32][CH3:33])=[O:31])[CH:24]=[CH:23]5)[CH:14]=[CH:15][C:16]=3[CH2:17][OH:18])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

3

Reactant 1

HCID 11797378HCID 11797378, compound

Product 1

HCID 10764915HCID 10764915, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6.2 g (0.014 mol) of the acid obtained in Example 10 are dissolved in 30 ml of THF and treated with 49 ml of BH3 (1M) in THF. The reaction medium is refluxed for 12 h, it is then evaporated, taken up in 900 ml of water and treated with 35 ml of 1N HCl. It is extracted with 800 ml of ethyl acetate, and the organic phase is washed with water and evaporated. The residue is chromatographed on silica in dichloromethane to give 4.45 g (75%) of the expected derivative which melts at 212° C.

Workup

  1. temperatureThe reaction medium is refluxed for 12 h
  2. customit is then evaporated
  3. additiontreated with 35 ml of 1N HCl
  4. extractionIt is extracted with 800 ml of ethyl acetate
  5. washthe organic phase is washed with water
  6. customevaporated
  7. customThe residue is chromatographed on silica in dichloromethane
  8. customto give 4.45 g (75%) of the expected derivative which melts at 212° C.

Sources & evidence

ORD record
ord-fec5bba93cf84eb4ad68f5a389322415
Source dataset
uspto-grants-1996_08
Patent number
US05547983

Reaction notes

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