Diethyl Malonate → 2-(Cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid diethyl ester

HRID 1789899Notes

Reaction equation

[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[C:14]([O:18][C:19](=[O:28])[NH:20][C@H:21]1[CH2:25][C@@H:24]([CH2:26]Br)[CH:23]=[CH:22]1)([CH3:17])([CH3:16])[CH3:15].CCOC(C)=O>CN(C=O)C>[CH2:10]([O:9][C:1](=[O:8])[CH:2]([CH2:26][C@H:24]1[CH2:25][C@@H:21]([NH:20][C:19]([O:18][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:28])[CH:22]=[CH:23]1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

Diethyl malonate (1.29 mL, 8.5 mmol) was added to a mixture of NaH (60%, 0.34 g; 8.5 mmol) in DMF (10 mL). After stirring at room temperature for 15 min a solution of cis-(4-bromomethyl-cyclopent-2-enyl)-carbamic acid tert-butyl ester (1.95 g, 7.1 mmol) in DMF (12 mL) was added, and the reaction mixture was stirred at 60° C. for 19 h. EtOAc was added and the organic phase was extracted with water and brine, dried and concentrated under reduced pressure to give 2.44 g of the crude product. Purification by flash chromatography (CH2Cl2/EtOAc: 1/0→68/32) afforded of 2-(cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid diethyl ester (1.47 g, 58%).

Workup

additionwas added
extractionthe organic phase was extracted with water and brine
customdried
concentrationconcentrated under reduced pressure
customto give 2.44 g of the crude product
customPurification by flash chromatography (CH2Cl2/EtOAc: 1/0→68/32)

Sources & evidence

ORD record: ord-01ef05968dd24c929b5741933b41a1aa
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071175B1

Reaction notes

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