(Diethylamino)trimethylsilane → Prostaglandin E2

HRID 1834051Notes

Reaction equation

HRID 1834051 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C@@H:12]([OH:23])[CH2:11][C@H:10]1[OH:24].C[Si](N(CC)CC)(C)C.C(OCC)(=O)C.CCCCCC>CC(C)=O.CCOCC>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:25])/[CH:7]=[CH:8]/[C@@H:9]1[C@@H:13]([CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:12](=[O:23])[CH2:11][C@H:10]1[OH:24]

Participants

6

Reactant 3

HCID 70454(Diethylamino)trimethylsilaneHCID 5280363DinoprostHCID 21226206Ethyl acetate hexane

Product 1

HCID 5280360Prostaglandin E2

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.07 g of PGF2=, 1,15-lactone in 45 ml of anhydrous acetone was cooled under nitrogen to between -45° and -40° and treated with 4.5 ml of trimethylsilyldiethylamine. After the addition was complete (2-3 min.), the mixture was stirred at -42° ± 2° C. for 2 hours, by which time TLC (25% ethyl acetate/hexane) showd only a trace of starting material. The reaction mixture was then cooled to -78° , diluted with 150 ml of precooled ether (-78° ) and poured into ice/brine. After extraction with hexane, the combined organic layers were washed with aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford the mono-trimethylsily derivative of PGE2α, 1,15-lactone.

Workup

  1. additionAfter the addition
  2. custom(2-3 min.)
  3. temperatureThe reaction mixture was then cooled to -78°
  4. extractionAfter extraction with hexane
  5. washthe combined organic layers were washed with aqueous sodium bicarbonate and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95d120d246ec41b88980988eedf6e03e
Source dataset
uspto-grants-1978_01
Patent number
US04067991

Reaction notes

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