Triethylamine → 1-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

HRID 522357

Reaction equation

HRID 522357 reaction equation
[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[OH:9])[CH2:2][CH2:3][CH:4]=[CH2:5].[CH2:10]1[C:15](=[O:16])[N:14]([O:17][C:18](ON2C(=O)CCC2=O)=[O:19])[C:12](=[O:13])[CH2:11]1.C(N(CC)CC)C>C(#N)C>[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[O:9][C:18]([O:17][N:14]1[C:15](=[O:16])[CH2:10][CH2:11][C:12]1=[O:13])=[O:19])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 67304189rel-(1R,2R)-2-(pent-4-en-1-yl)cyclopropan-1-ol

Product 1

HCID 895908351-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (1R,2R)-2-(pent-4-en-1-yl)cyclopropanol (see International Patent Application Publication No. WO 08/057209) (17.1 g) in acetonitrile (193 mL) was added N,N′-disuccinimidyl carbonate (49.3 g) then triethylamine (53.7 mL) The mixture was heated to 40° C. for 18 hours. The reaction mixture was cooled to room temperature and the solids were removed by filtration. The solvent was removed in vacuo. The residue was purified by flash chromatography (ISCO, 10 to 70% ethyl acetate in hexanes) to give the desired product (18 g). 1H NMR (500 MHz, CDCl3): δ (ppm) 4.06-4.03 (m, 1H), 2.87 (s, 4H), 2.28-2.25 (m, 2H), 1.98-1.97 (m, 1H), 1.72-1.63 (m, 2H), 1.44-1.39 (m, 2H), 1.30-1.25 (m, 1H), 1.12-1.08 (m, 1H), 0.72-0.68 (m, 1H).

Workup

  1. customthe solids were removed by filtration
  2. customThe solvent was removed in vacuo
  3. customThe residue was purified by flash chromatography (ISCO, 10 to 70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2fbb07a12b844ce7b8c488083552361b
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Linked notes

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