METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE → Methyl 7-{(3R)-3-[(oxan-2-yl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoate

HRID 1439803Notes

Reaction equation

[OH:1][C@@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1.O[C@H]1CC(=O)C(CCC[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=O)=C1>>[O:33]1[CH2:34][CH2:28][CH2:29][CH2:30][CH:31]1[O:1][C@@H:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:3]1

Participants

Reactant 2

HCID 10800078METHYL (R)-(+)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE

HCID 10823960Norprostol, (-)-

Product 1

HCID 13216834Methyl 7-{(3R)-3-[(oxan-2-yl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoate

Procedure

Substitution of an equivalent quantity of methyl 7-(3(R)-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate for the methyl 7-(3(S)-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate and substantial repetition of the procedure detailed above affords methyl 7-(3(R)-tetrahydropyran-2-yloxy-5-oxocyclopent-1-en-1-yl)heptanoate.

Sources & evidence

ORD record: ord-6331347f8f99434cb8de5d2fa19952ab
Source dataset: uspto-grants-1977_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04060691

Reaction notes

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