Triphenylphosphine → (3S,4R)-3-methyl-4-(4-phenylbutyl)oxetan-2-one

HRID 1107151Notes

Reaction equation

HRID 1107151 reaction equation
O[C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@H:3]([CH3:7])[C:4]([OH:6])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=C(SSC2N=CC=CC=2)N=CC=1>C(Cl)(Cl)Cl.C(#N)C.CS([O-])(=O)=O.[Hg+2].CS([O-])(=O)=O>[CH3:7][C@H:3]1[C@@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:5][C:4]1=[O:6]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfideHCID 57188911(+)-(2S, 3R)-3-hydroxy-2-methyl-7-phenylheptanoic acid

Product 1

HCID 57048705(3S,4R)-3-methyl-4-(4-phenylbutyl)oxetan-2-oneYield 66%

Reagents, catalysts & solvents 3

HCID 10992809Mercury(II) methanesulfonateCatalystHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
48 °C

Procedure

(+)-(2S, 3R)-3-Hydroxy-2-methyl-7-phenylheptanoic acid is added to a solution of triphenylphosphine (0.88 g, 3.4 mmol) and 2,2'-dipyridyl disulfide (0.7 g, 3.2 mmol) in chloroform (20 mL) and is stirred for 20 minutes. Mercury(II) methanesulfonate (1.6 g, 4.2 mmol) is suspended in acetonitrile (52 mL), warmed to 48° C. and the activated ester/chloroform solution is added over 5 minutes. This mixture is heated for 1 minute after completion of the addition and then cooled. The mixture is filtered through Celite, the filtrate concentrated in vacuo and the residue is purified by column chromatography (silica, 25% ether in petroleum ether) to yield (3S,4R)-3-methyl-4-(4-phenylbutyl)oxetan-2-one (0.3 g, 66%). 1H NMR (300 MHz, CDCl3) δ 7.31-7.26 (m, 2H), 7.21-7.15 (m, 3H), 4.19-4.13 (m, 1H), 3.25-3.16 (m, 1H), 2.64 (t, J=7.6 Hz, 2H), 1.95-1.64 (m, 4H), 1.55-1.40 (m, 5H), 1.37 (d, J=7.5 Hz, 3H).

Workup

  1. temperatureThis mixture is heated for 1 minute
  2. additionafter completion of the addition
  3. temperaturecooled
  4. filtrationThe mixture is filtered through Celite
  5. concentrationthe filtrate concentrated in vacuo
  6. customthe residue is purified by column chromatography (silica, 25% ether in petroleum ether)

Sources & evidence

ORD record
ord-000dc22e19ea493bb91d95b8f4b494fe
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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