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

HRID 522361

Reaction equation

[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[OH:9])[CH2:2][CH2:3][CH:4]=[CH2:5].N1C=CC=CC=1.[CH2:16]1[C:21](=[O:22])[N:20]([O:23][C:24](ON2C(=O)CCC2=O)=[O:25])[C:18](=[O:19])[CH2:17]1>C(#N)C.CN(C1C=CN=CC=1)C.CCOCC>[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[O:9][C:24]([O:23][N:20]1[C:21](=[O:22])[CH2:16][CH2:17][C:18]1=[O:19])=[O:25])[CH2:2][CH2:3][C:4]#[CH:5]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of (1R,2R)-2-(pent-4-en-1-yl)cyclopropanol (See International Patent Application Publication No. WO08/057209) (2.13 g; 70% wt) in acetonitrile (20 ml) was added pyridine (1.5 ml), followed by N,N′-disuccinimidyl carbonate (3.74 g) and a crystal of DMAP. The mixture was stirred at 40° C. overnight. After cooling to room temperature, the reaction mixture was diluted with ether and washed with HCl 1N, water and brine and dried over sodium sulfate. The organic layer was filtered and concentrated to provide the desired product (2.88 g) as an oil. 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), 1.72-1.65 (m, 2H), 1.46-1.40 (m, 2H), 1.31-1.24 (m, 1H), 1.12-1.08 (m, 1H), 0.72-0.68 (m, 1H).

Workup

temperatureAfter cooling to room temperature
washwashed with HCl 1N, water and brine
dry with materialdried over sodium sulfate
filtrationThe organic layer was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-a462f20ee0eb40e099a1e0ec74193af1
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328138B2

Linked notes

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