Triphenylphosphine → (2S,3S)-3-pentyloxiran-2-ylmethyl 2-fluoro-6-(4-octyloxyphenyl)pyridin-3-yl ether

HRID 1780576Notes

Reaction equation

HRID 1780576 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:32][C:33]1[C:38]([OH:39])=[CH:37][CH:36]=[C:35]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[CH:42][CH:41]=2)[N:34]=1.[CH2:55]([C@@H:60]1[O:62][C@H:61]1[CH2:63]O)[CH2:56][CH2:57][CH2:58][CH3:59]>O1CCCC1>[F:32][C:33]1[C:38]([O:39][CH2:63][C@H:61]2[C@H:60]([CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[O:62]2)=[CH:37][CH:36]=[C:35]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[CH:42][CH:41]=2)[N:34]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10888033HCID 10888033, compoundHCID 190469612-(4-Octyloxyphenyl)-5-hydroxy-6-fluoropyridine

Product 1

HCID 57119562(2S,3S)-3-pentyloxiran-2-ylmethyl 2-fluoro-6-(4-octyloxyphenyl)pyridin-3-yl etherYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.44 g (2.55 mmol) of diethyl azodicarboxylate is added dropwise at 0° C. to 0.67 g (2.55 mmol) of triphenylphosphine in 15 ml of tetrahydrofuran, and the mixture is stirred at room temperature for 30 minutes. 0.54 g (1.70 mmol) of 2-fluoro-3-hydroxy-6-(4-octyloxyphenyl)pyridine (prepared by EXAMPLE 3) and 0.25 g (1.70 mmol) of (2S,3S)-3-pentyl-2-oxiranylmethanol are then added. After a reaction time of 18 hours at room temperature, the solvent is distilled off, and the residue is purified by chromatography (silica gel, 8:2hexane/ethyl acetate ). Recrystallization from 8:2hexane/ethyl acetate gives 0.28 g of (2S,3S)-3-pentyloxiran-2-ylmethyl 2-fluoro-6-(4-octyloxyphenyl)pyridin-3-yl ether having an [α]D° (2.4% in CH2Cl2) of -15.75°. ##STR70##

Workup

  1. distillationAfter a reaction time of 18 hours at room temperature, the solvent is distilled off
  2. customthe residue is purified by chromatography (silica gel, 8:2hexane/ethyl acetate )
  3. customRecrystallization from 8:2hexane/ethyl acetate

Sources & evidence

ORD record
ord-93eead93b33645e29651a5ecb29681fb
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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