Triphenylphosphine → HCID 54031575, compound

HRID 440729Notes

Reaction equation

HRID 440729 reaction equation
N(C(OC(C)C)=O)=NC([O:5][CH:6]([CH3:8])C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@@H:35]1[CH2:52][CH2:51][C@@:50]2([CH3:53])[C:37]([CH2:38][CH2:39][C@@H:40]3[C@@H:49]2[CH2:48][CH2:47][C@@:45]2([CH3:46])[C@H:41]3[CH2:42][CH2:43][C:44]2=[O:54])=[CH:36]1.[S:55]1C=CC=C1CC(O)=O>O1CCCC1>[C:6]([S:55][C@H:35]1[CH2:52][CH2:51][C@@:50]2([CH3:53])[C:37]([CH2:38][CH2:39][C@@H:40]3[C@@H:49]2[CH2:48][CH2:47][C@@:45]2([CH3:46])[C@H:41]3[CH2:42][CH2:43][C:44]2=[O:54])=[CH:36]1)(=[O:5])[CH3:8]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 69147632791-99-3

Product 1

HCID 54031575HCID 54031575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropyl azodicarboxylate (3.3 ml) was added to a solution of 4.5 g of triphenylphosphine in 90 ml of tetrahydrofuran at 0 ° C. and the mixture was stirred for 30'. To this mixture a solution of 2.1 g of 3α-hydroxy-androst-4-en-17-one (D'Incan E., Tetrahedron, 1982, 38, 1755) and 2.1 ml of thiolacetic acid in 90 ml of tetrahydrofuran was added dropwise and the residue was stirred for 1 hr at room temperature. The solvent was evaporated to dryness under reduced pressure and the crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 95/5 as eluant to give 1.4 g of the title compound (IV-a) as a white solid.

Workup

  1. stirringthe residue was stirred for 1 hr at room temperature
  2. customThe solvent was evaporated to dryness under reduced pressure
  3. customthe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-9beae95fc85b42fca86754a7d2df101b
Source dataset
uspto-grants-1996_05
Patent number
US05521167

Reaction notes

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