2-Propylvaleryl chloride → HCID 18666270, compound

HRID 2399964Notes

Reaction equation

HRID 2399964 reaction equation
[CH2:1]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5](Cl)=[O:6])[CH2:2][CH3:3].[Si:11]([O:18][C@H:19]1[CH2:28][C@H:27]([OH:29])[C@H:26]2[C:21]([CH:22]=[CH:23][C@H:24]([CH3:47])[C@@H:25]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:33]2)=[CH:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]>N1C=CC=CC=1.C(OCC)(=O)C.N1(C2C=CN=CC=2)CCCC1>[Si:11]([O:18][C@H:19]1[CH2:28][C@H:27]([O:29][C:5](=[O:6])[CH:4]([CH2:8][CH2:9][CH3:10])[CH2:1][CH2:2][CH3:3])[C@H:26]2[C:21]([CH:22]=[CH:23][C@H:24]([CH3:47])[C@@H:25]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:41])[CH3:42])[CH2:33]2)=[CH:20]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:13])[CH3:12]

Participants

6

Reactant 2

HCID 762402-Propylvaleryl chlorideHCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether

Product 1

HCID 18666270HCID 18666270, compoundYield 94.4%

Reagents, catalysts & solvents 3

HCID 755674-PyrrolidinopyridineCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

15 mg (0.1 mmol) of 4-(1-pyrrolidinyl)pyridine and 592 mg (3.6 mmol) of 2-propylvaleryl chloride were added to a solution of 1.0 g (1.8 mmol) of (4R,6R)-6-{2[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-hydroxy-2-methyl-1-naphthyl]ethyl}-tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example B, above] in 5 ml of dry pyridine, whilst ice-cooling, and the resulting mixture was stirred at 70° C. for 3 hours. At the end of this time, the reaction mixture was diluted with 100 ml of ethyl acetate, and the diluted mixture was then washed with 100 ml of water, 100 ml of a 10% w/v aqueous solution of hydrogen chloride, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, in that order. The organic layer was then dried over anhydrous magnesium sulfate, after which this layer was removed by filtration. The resulting filtrate was concentrated by evaporation under reduced pressure and the residue obtained was purified by flash column chromatography through silica gel, using a 5:1 by volume mixture hexane and ethyl acetate as the eluent, to give 1.15 g (93% yield) of the title compound.

Workup

  1. customprepared
  2. washthe diluted mixture was then washed with 100 ml of water, 100 ml of a 10% w/v aqueous solution of hydrogen chloride
  3. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  4. customafter which this layer was removed by filtration
  5. concentrationThe resulting filtrate was concentrated by evaporation under reduced pressure
  6. customthe residue obtained
  7. customwas purified by flash column chromatography through silica gel

Sources & evidence

ORD record
ord-410cd6dd945e4e53afa7a8a915459b77
Source dataset
uspto-grants-1995_09
Patent number
US05451688

Reaction notes

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