Dabco → HCID 76608224, compound

HRID 2099919Notes

Reaction equation

[C:1]1([P:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:8]2[CH2:16][C@@H:11]3[O:12][C:13](=[O:15])[CH2:14][C@@H:10]3[C@H:9]2[CH2:17][P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.C1N2CCN(CC2)C1>C1(C)C=CC=CC=1>[C:31]1([P:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]2[CH2:16][CH:11]3[O:12][C:13](=[O:15])[CH2:14][CH:10]3[CH:9]2[CH2:17][P:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a 25 mL-recovery flask were added (3aR,4S,5S,6aS)-(5-diphenylphosphanyl-4-[(diphenylphosphanyl)methyl]hexahydrocyclopenta[b]furan-2-one-borane complex (Compound 3, 1.0 mmol) and 1,4-diazobicyclo[2,2,2]octane (DABCO, 0.25 g, 2.2 mmol), and the atmosphere in the flask was substituted with nitrogen. The mixture was added with 10 mL of deoxygenized toluene, and stirred at 40° C. for 3 hours. The solvent was concentrated in an evaporator, and the residue was purified by silica gel column chromatography (toluene/ethyl acetate=20/1 to 4/1) to obtain (3aR,4S,5S,6aS)-(5-diphenylphosphanyl-4-[(diphenylphosphanyl)methyl]hexahydrocyclopenta[b]furan-2-one (CLPL-S, yield: 85%).

Workup

concentrationThe solvent was concentrated in an evaporator
customthe residue was purified by silica gel column chromatography (toluene/ethyl acetate=20/1 to 4/1)

Sources & evidence

ORD record: ord-30c0f76486f84fbdb20c72eb05d7f882
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07569730B2

Reaction notes

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