Toluene → HCID 68541392, compound

HRID 1432086Notes

Reaction equation

[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]([CH:15]1[CH:19]=[CH:18][C:17](=[O:20])[O:16]1)[CH2:9][CH:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])([CH3:4])([CH3:3])[CH3:2].[C:22]1(C)C=CC=CC=1>C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu].[Cu].[Cu].[Cu].[Cu].[Cu]>[C:1]([O:5][C:6](=[O:21])[NH:7][C@@H:8]([CH:15]1[CH2:19][CH:18]([CH3:22])[C:17](=[O:20])[O:16]1)[CH2:9][CH:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 25 °C

Procedure

Under nitrogen atmosphere to 20 ml thoroughly degassed toluene are subsequently added 0.63 g (0.31 mmol) hydrido(triphenylphosphine)copper(I) hexamer, 2.9 ml polymethylhydrosiloxane and a (degassed) solution of 5.7 g (19.3 mmol) [(R)-3-methyl-1-(5-oxo-2,5-dihydro-furan-2-yl)hex-5-enyl]-carbamic acid tert-butyl ester in toluene. After stirring for 2 h at 25° C. 6 mg (0.01 mmol) of R(+)-2,2′-bis-(diphenylphosphino)-6,6′-dimethoxy-1,1-biphenyl are added as an accelerating ligand for the copper complex. After 12 h the mixture is diluted with ethyl acetate and washed with water, 5% aqueous citric acid and 5% aqueous NaHCO3. Chromatography on silica gel (EtOAc/hexane 1:9, then 1:3) provides the title compound as a diastereomeric mixture.

Workup

washwashed with water, 5% aqueous citric acid and 5% aqueous NaHCO3

Sources & evidence

ORD record: ord-ac0e27964e5c4e1ea7fff8814c5649ed
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612055B2

Reaction notes

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