Norprostol → Methyl 7-(5-oxo-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopent-1-en-1-yl)heptanoate

HRID 1439804Notes

Reaction equation

[OH:1][CH: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][CH: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 3912664Norprostol

HCID 10823960Norprostol, (-)-

Product 1

HCID 13216833Methyl 7-(5-oxo-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopent-1-en-1-yl)heptanoate

Procedure

When an equivalent quantity of methyl 7-(3(RS)-hydroxy-5-oxocyclopent-1-en--yl)heptanoate is substituted for the methyl 7-(3(S)-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate and the procedure detailed in Part A substantially repeated, there is obtained methyl 7-(3(RS)-tetrahydropyran-2-yloxy-5-oxocyclopent-1-en-1-yl)heptanoate.

Sources & evidence

ORD record: ord-b0e609de5ad649dbbc660dc53d305c47
Source dataset: uspto-grants-1977_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04060691

Reaction notes

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