Vinylcyclopentane → (3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-one

HRID 1670428

Reaction equation

HRID 1670428 reaction equation
[OH:1][C@@H:2]1[C@H:6]([C@H:7]([OH:10])[CH:8]=[CH2:9])[O:5][C:4](=[O:11])[C@@H:3]1[O:12][CH3:13].C([CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=C>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.C(Cl)Cl>[CH:16]1(/[CH:9]=[CH:8]/[C@H:7]([C@@H:6]2[O:5][C:4](=[O:11])[C@H:3]([O:12][CH3:13])[C@@H:2]2[OH:1])[OH:10])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 77345VinylcyclopentaneHCID 67241097(3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-one

Product 1

HCID 57463784(3R,4R,5S)-5-[(1R,2E)-3-cyclopentyl-1-hydroxyprop-2-en-1-yl]-4-hydroxy-3-methoxydihydrofuran-2(3H)-oneYield 51%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

2 g of 31 (10.63 mmol), 4.22 g of vinylcyclopentane (43.92 mmol), 80 mL of CH2Cl2 and 226 mg of 2nd generation Grubb's catalyst (C46H65Cl2N2PRu, MW 848.98, 0.266 mmol) are added to a 250 mL round-bottomed flask. The medium is stirred for 2 h at RT and then heated for 4 h at 45° C. The insoluble material is filtered and then the solvent is evaporated and the crude product (3.39 g) is chromatographed on a silica cartridge (150 g), eluting with a heptane/AcOEt (50/50) mixture. 1.39 g of expected product 32 (white solid) are obtained.

Workup

  1. temperatureheated for 4 h at 45° C
  2. filtrationThe insoluble material is filtered
  3. customthe solvent is evaporated
  4. customthe crude product (3.39 g) is chromatographed on a silica cartridge (150 g)
  5. washeluting with a heptane/AcOEt (50/50) mixture

Sources & evidence

ORD record
ord-051f1945619d4cfcb76a808bc8be29b8
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Linked notes

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