Cyanomethylenetributylphosphorane → HCID 89633502, compound

HRID 1502055Notes

Reaction equation

[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH:10](O)[CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@H:13]3[CH2:25][OH:26])[CH:7]=[CH:6][C:5]=12.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[N:1]1[O:2][N:3]=[C:4]2[CH:9]=[C:8]([CH:10]3[O:26][CH2:25][C@@H:13]4[CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:16][CH2:17][N:12]4[CH2:11]3)[CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 100 °C

Procedure

To a 20 mL size microwave tube containing a stir bar was added tert-butyl (3S)-4-[2-(2,1,3-benzoxadiazol-5-yl)-2-hydroxyethyl]-3-(hydroxymethyl)piperazine-1-carboxylate (0.80 g, 2.1 mmol), cyanomethylene tri-n-Butylphosphorane (0.92 g, 3.8 mmol) and anhydrous toluene (15 mL). The tube was degassed and purged with N2 followed by heating at 100° C. for 12 h. The solution was concentrated to dryness and the organic residue was then purified over silica gel with the solvent systems of 30% Acetone in DCM to furnish the title compound: 1H-NMR (CDCl3, 500 MHz), δ 7.854-7.832 (m, 2H), 7.428 (d, J=9 Hz, 1H), 4.754 (d, J=10.5 Hz, 1H), 4.041-4.015 (m, 3H), 3.774-3.733 (m, 2H), 3.517 (t, J=11 Hz, 1H), 3.011 (d, J=11.5 Hz, 1H), 2.782 (d, J=9.5 Hz, 1H), 2.335-2.240 (m, 3H), 1.510 (s, 9H).

Workup

additionTo a 20 mL size microwave tube containing a stir bar
customThe tube was degassed
custompurged with N2
concentrationThe solution was concentrated to dryness
customthe organic residue was then purified over silica gel with the solvent systems of 30% Acetone in DCM

Sources & evidence

ORD record: ord-e7b8dc69423444c383003892f79c0d25
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206199B2

Reaction notes

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