Formaldehyde → 2-(cis-4-Tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-acrylic acid ethyl ester

HRID 1789901Notes

Reaction equation

HRID 1789901 reaction equation
C(NCC)C.[CH2:6]([O:8][C:9](=[O:28])[CH:10]([CH2:14][C@H:15]1[CH2:19][C@@H:18]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:17]=[CH:16]1)[C:11](O)=O)[CH3:7].C=O.C(Cl)Cl>O>[CH2:6]([O:8][C:9](=[O:28])[C:10]([CH2:14][C@H:15]1[CH2:19][C@@H:18]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:17]=[CH:16]1)=[CH2:11])[CH3:7]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 8021DiethylamineHCID 696503392-(cis-4-Tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid monoethyl ester

Product 1

HCID 696502532-(cis-4-Tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-acrylic acid ethyl esterYield 94.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethyl amine (0.31 mL; 3.0 mmol) was added to a mixture of 2-(cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-malonic acid monoethyl ester (0.66 g, 2.0 mmol) in 36% aqueous solution of formaldehyde (0.25 mL, 3.2 mmol), CH2Cl2 (1.6 mL) and water (1.6 mL) at 0° C. The reaction mixture was stirred at room temperature overnight, poured onto ice-water (400 mL) and extracted with CH2Cl2. During the extraction, phase separation was improved by the addition of brine. The combined organic phases were washed with 5% NaHCO3, dried and concentrated under reduced pressure to yield 2-(cis-4-tert-butoxycarbonylamino-cyclopent-2-enylmethyl)-acrylic acid ethyl ester (0.56 g, 94%) as an oil.

Workup

  1. additionpoured onto ice-water (400 mL)
  2. extractionextracted with CH2Cl2
  3. extractionDuring the extraction, phase separation
  4. additionwas improved by the addition of brine
  5. washThe combined organic phases were washed with 5% NaHCO3
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6cc91569459a484089d3ec720f658960
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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