Triethylamine → Cyclopropylmethyl 2,5-dioxopyrrolidin-1-yl carbonate

HRID 1468815Notes

Reaction equation

HRID 1468815 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[C:6](=O)([O:15]N1C(=O)CCC1=O)[O:7][N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14].C(N(CC)CC)C>C(#N)C>[C:6](=[O:15])([O:7][N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14])[O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75644CyclopropanemethanolHCID 676246Di(succinimido) carbonate

Product 1

HCID 57747023Cyclopropylmethyl 2,5-dioxopyrrolidin-1-yl carbonateYield 108.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of cyclopropylmethanol (1.0 g, 13.8 mmol) in acetonitrile (15 mL) was added bis(2,5-dioxopyrrolidin-1-yl) carbonate (7.1 g, 27.7 mmol) and triethylamine (5.8 mL, 41.6 mmol). The reaction was stirred overnight, then quenched with saturated NaHCO3 solution (aq.) and extracted with ethyl acetate (3×50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound (3.2 g, quant.) as an amber oil: 1H NMR (300 MHz, CDCl3) δ 4.16 (d, J=7.5 Hz, 2H), 2.84 (s, 4H), 1.26 (m, 1H), 0.70-0.64 (m, 2H), 0.40-0.35 (m, 2H).

Workup

  1. customquenched with saturated NaHCO3 solution (aq.)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8de73bc45544ab2b3385390e5cfb067
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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