Hexane → Methyl 3-(3-oxocyclopentyl)propanoate

HRID 991968

Reaction equation

HRID 991968 reaction equation
CC1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.[CH3:51][O:52][C:53](=[O:62])[CH2:54][CH2:55][C:56]1[CH2:60][CH2:59][C:58](=[O:61])[CH:57]=1.CCCCCC>C(OCC)(=O)C>[CH3:51][O:52][C:53](=[O:62])[CH2:54][CH2:55][CH:56]1[CH2:60][CH2:59][C:58](=[O:61])[CH2:57]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 4189906(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1, 1'-binaphthylHCID 111828433-(3-Oxo-cyclopent-1-enyl)-propionic acid methyl ester

Product 1

HCID 301170Methyl 3-(3-oxocyclopentyl)propanoateYield 88.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

General procedure B using (S)-p-tol-BINAP and 3-(3-oxo-cyclopent-1-enyl)-propionic acid methyl ester (0.084 g, 0.5 mmol) gave, after 24 h at 0° C. and flash chromatography (4:1, then 2:1 hexane:ethyl acetate), the title compound as a clear oil (0.075 g, 88% yield). Spectroscopic data were consistent with previously reported data for this compound.15 [α]D25° C.−112° (c 1.3, CHCl3). Conversion of the title compound to the corresponding benzyl ester followed by chiral HPLC analysis (Chiracel OD column) indicated that the title compound was obtained in 91% ee.

Workup

  1. customgave, after 24 h at 0° C.

Sources & evidence

ORD record
ord-b508e9f183bd4b45bed41e5665cebdc5
Source dataset
uspto-grants-2002_10
Patent number
US06465664B1

Linked notes

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