Triethylamine → 2,5-Dioxopyrrolidin-1-yl 1-methylcyclopropyl carbonate

HRID 2405807Notes

Reaction equation

HRID 2405807 reaction equation
[CH3:1][C:2]1([OH:5])[CH2:4][CH2:3]1.[O:6]=[C:7]1[CH2:11][CH2:10][C:9](=[O:12])[N:8]1[O:13][C:14](=O)[O:15]N1C(=O)CCC1=O.C(N(CC)CC)C>C(#N)C.CCOC(C)=O>[CH3:1][C:2]1([O:5][C:14](=[O:15])[O:13][N:8]2[C:9](=[O:12])[CH2:10][CH2:11][C:7]2=[O:6])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 115644661-Methylcyclopropan-1-ol

Product 1

HCID 577528092,5-Dioxopyrrolidin-1-yl 1-methylcyclopropyl carbonateYield 19.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-methyl-cyclopropanol (1.25 g, 17.4 mmol) in acetonitrile (44 mL) was added carbonic acid bis-(2,5-dioxo-pyrrolidin-1-yl)ester (6.68 g, 26.1 mmol) and triethylamine (7.3 mL, 52.3 mmol). The reaction was stirred at room temperature for 21 h. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3 (2×) and brine. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica (15→50%→100% Hex/EtOAc) to provide carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 1-methyl-cyclopropyl ester (722.8 mg, 19%): 1H NMR (CDCl3, 300 MHz) δ 2.83 (s, 4H), 1.63 (s, 3H), 1.10 (m, 2H), 0.73 (m, 2H).

Workup

  1. washwashed with saturated aqueous NaHCO3 (2×) and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography on silica (15→50%→100% Hex/EtOAc)

Sources & evidence

ORD record
ord-a74205bd391742dd914178856c4897f1
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

Loading…