Pyridine → 7-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-chlorobutyrate

HRID 1172023Notes

Reaction equation

HRID 1172023 reaction equation
[OH:1][CH:2]1[CH:6]2[O:7][C:8](=[O:15])[CH:9]3[CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH:3]1[CH2:4][CH:5]23.[Cl:16][CH2:17][CH2:18][CH2:19][C:20](Cl)=[O:21].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:16][CH2:17][CH2:18][CH2:19][C:20]([O:1][CH:2]1[CH:6]2[O:7][C:8](=[O:15])[CH:9]3[CH:10]([C:11]([O:13][CH3:14])=[O:12])[CH:3]1[CH2:4][CH:5]23)=[O:21]

Participants

6

Reactant 4

HCID 1049PyridineHCID 783704-Chlorobutyryl chlorideHCID 516892Sodium BicarbonateHCID 15601184Methyl 6-hydroxy-2-oxohexahydro-3,5-methano-2h-cyclopenta-[b]furan-7-carboxylate

Product 1

HCID 578671007-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 4-chlorobutyrateYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 180 ml of tetrahydrofuran were dissolved 21.2 g of methyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta-[b]furan-7-carboxylate and 16.9 g of 4-chlorobutyric acid chloride. To the solution below 20° C., 9.10 g of pyridine was added dropwise. The solution was stirred at room temperature for 1 hour and combined with 40 g of a 5% aqueous solution of sodium hydrogen carbonate, followed by ordinary work-up. There was obtained 30.4 g of a crude product (crude yield 96%).

Sources & evidence

ORD record
ord-4456801942a345148fc2c7e28d5b2178
Source dataset
uspto-grants-2010_11
Patent number
US07833694B2

Reaction notes

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