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

HRID 252897Notes

Reaction equation

HRID 252897 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][C:18](Cl)=[O:19].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:16][CH2:17][C:18]([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:19]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 15601184Methyl 6-hydroxy-2-oxohexahydro-3,5-methano-2h-cyclopenta-[b]furan-7-carboxylate

Product 1

HCID 578958527-methoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-chloroacetateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 180 ml of tetrahydrofuran were dissolved 25.0 g of methyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta-[b]furan-7-carboxylate and 16.0 g of 2-chloroacetic acid chloride. To the solution below 20° C., 10.7 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 post-treatment. Recrystallization from isopropyl ether gave 31.5 g of the target compound (yield 93%).

Workup

  1. customRecrystallization from isopropyl ether

Sources & evidence

ORD record
ord-39f5a7db5d584be9a4812281a0885b59
Source dataset
uspto-grants-2011_01
Patent number
US07871752B2

Reaction notes

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