Dichloromethane → (s)-tert-Butyl 2-cyclopropyl-3,5-dioxopyrrolidine-1-carboxylate

HRID 1011599Notes

Reaction equation

HRID 1011599 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:13]1[CH2:15][CH2:14]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1(C)OC(=O)CC(=O)[O:18]1.C(Cl)Cl.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH:13]1([C@H:9]2[C:10](=[O:12])[CH2:16][C:17](=[O:18])[N:8]2[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 224921462-(Tert-butoxycarbonylamino)-2-cyclopropylacetic acid

Product 1

HCID 57659759(s)-tert-Butyl 2-cyclopropyl-3,5-dioxopyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(tert-Butoxycarbonylamino)-2-cyclopropylacetic acid (13) (5.47 g, 25.4 mmol), Meldrum's acid (14) (4.02 g, 27.9 mmol), and DMAP (4.34 g, 35.56 mmol) were added to CH2Cl2 (100 mL) under nitrogen at 0° C. After 30 minutes EDAC (6.81 g, 35.56 mmol) was added. The reaction was stirred 16 hr at rt and poured into EtOAc (300 mL), washed with brine (200 ml), 5% citric acid (300 mL), and again brine (200 mL). The organic phase was then refluxed for 1 hr. The mixture was evaporated to give (S)-tert-butyl 2-cyclopropyl-3,5-dioxopyrrolidine-1-carboxylate (15) a yellow oil (4.0 g, 69%) that was taken into the next reaction without further purification.

Workup

  1. washwashed with brine (200 ml), 5% citric acid (300 mL), and again brine (200 mL)
  2. temperatureThe organic phase was then refluxed for 1 hr
  3. customThe mixture was evaporated

Sources & evidence

ORD record
ord-c2d6b44d8ea54d2386b2d38ec96928f7
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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