Water → 7-tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-chloroacetate

HRID 558050Notes

Reaction equation

HRID 558050 reaction equation
[OH:1][CH:2]1[CH:6]2[O:7][C:8](=[O:18])[CH:9]3[CH:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]1[CH2:4][CH:5]23.[Cl:19][CH2:20][C:21](Cl)=[O:22].N1C=CC=CC=1.O>O1CCCC1>[Cl:19][CH2:20][C:21]([O:1][CH:2]1[CH:6]2[O:7][C:8](=[O:18])[CH:9]3[CH:10]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH:3]1[CH2:4][CH:5]23)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 57824120HCID 57824120, compound

Product 1

HCID 579457837-tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl 2-chloroacetateYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 1,000 ml of tetrahydrofuran were dissolved 163 g of tert-butyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-7-carboxylate and 86.9 g of 2-chloroacetic chloride. To this solution below 15° C., 58.3 g of pyridine was added dropwise. The reaction solution was stirred at room temperature for 2 hours, whereupon 250 ml of deionized water was added, followed by ordinary workup. Recrystallization from hexane yielded 200 g of the title compound. Yield 94%.

Workup

  1. additionwas added
  2. customRecrystallization from hexane

Sources & evidence

ORD record
ord-1183ecba70684630bc79b75dcc92f2cb
Source dataset
uspto-grants-2011_11
Patent number
US08062831B2

Reaction notes

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