Triethylamine → HCID 15285943, compound

HRID 400137Notes

Reaction equation

HRID 400137 reaction equation
C(N(CC)CC)C.N1(C2C=CN=CC=2)CCCC1.[CH2:19]([C:21]([CH3:27])([CH2:25][CH3:26])[C:22](Cl)=[O:23])[CH3:20].[Si:28]([O:35][C@H:36]1[CH2:45][C@H:44]([OH:46])[C@H:43]2[C:38]([CH:39]=[CH:40][C@H:41]([CH3:64])[C@@H:42]2[CH2:47][CH2:48][C@H:49]2[O:54][C:53](=[O:55])[CH2:52][C@H:51]([O:56][Si:57]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:59])[CH3:58])[CH2:50]2)=[CH:37]1)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>C1C=CC=CC=1.C(OCC)(=O)C>[Si:28]([O:35][C@H:36]1[CH2:45][C@H:44]([O:46][C:22](=[O:23])[C:21]([CH2:25][CH3:26])([CH3:27])[CH2:19][CH3:20])[C@H:43]2[C:38]([CH:39]=[CH:40][C@H:41]([CH3:64])[C@@H:42]2[CH2:47][CH2:48][C@H:49]2[O:54][C:53](=[O:55])[CH2:52][C@H:51]([O:56][Si:57]([C:60]([CH3:63])([CH3:62])[CH3:61])([CH3:58])[CH3:59])[CH2:50]2)=[CH:37]1)([C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:30])[CH3:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 11116219Butanoyl chloride, 2-ethyl-2-methyl-HCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether

Product 1

HCID 15285943HCID 15285943, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.76 ml (5.4 mmol) of triethylamine, 807 mg (5.4 mmol) of 4-(1-pyrrolidinyl)pyridine and 674 mg (4.5 mmol) of 2-ethyl-2-methylbutyryl chloride were added to a solution of 500 mg (0.91 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 10 ml of benzene and the resulting mixture was heated under reflux for 5 hours. At the end of this time, the reaction mixture was diluted with 50 ml of ethyl acetate. The diluted mixture was then washed with 30 ml of water, 30 ml of a 10% w/v aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, in that order. The organic phase was then dried over anhydrous magnesium sulfate, after which this phase was filtered. The filtrate was concentrated by evaporation under reduced pressure and the concentrate was purified by flash column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 601 mg (100% yield) of the title compound.

Workup

  1. customprepared
  2. temperatureunder reflux for 5 hours
  3. washThe diluted mixture was then washed with 30 ml of water, 30 ml of a 10% w/v aqueous solution of citric acid
  4. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  5. filtrationafter which this phase was filtered
  6. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  7. customthe concentrate was purified by flash column chromatography through silica gel
  8. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-d8027d269e444297a0a7b69585febbd6
Source dataset
uspto-grants-1998_10
Patent number
US05827855

Reaction notes

Loading…