3,3,3-Trifluoropropyne → HCID 66523230, compound

HRID 2284438Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N+:14]2=[N:17]O[C:19]([O-])=[C:13]2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(N1CCNC(C(O)=O)C1)=O)C1C=CC=CC=1.[F:40][C:41]([F:45])([F:44])[C:42]#C>CC1C=CC=CC=1C>[F:40][C:41]([F:45])([F:44])[C:42]1[CH:19]=[C:13]2[CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:16][CH2:15][N:14]2[N:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

5-[(Benzyloxy)carbonyl]-4,5,6,7-tetrahydro[1,2,3]oxadiazolo[3,4-a]pyrazin-8-ium-3-olate (C58, prepared from 4-[(benzyloxy)carbonyl]piperazine-2-carboxylic acid using the general procedure described by T. S. Mansour et al., 2006, PCT Intl. Appl. WO 2006/130588) (65 g, 0.24 mol) was dissolved in o-xylene (250 mL) and cooled to −78° C. in a bomb reactor. 3,3,3-Trifluoroprop-1-yne (25 g, 0.27 mol) was injected into the reaction mixture, and the bomb was heated to 270° C. for 24 hours. After cooling to room temperature, the reaction was concentrated in vacuo, and the residue was purified by silica gel chromatography to provide C60 as white crystals. Yield: 7.5 g, 23 mmol, 10%. [The major regioisomer, benzyl 2-(trifluoromethyl)-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxylate (C59), was also isolated, in 61% yield.]

Workup

temperaturethe bomb was heated to 270° C. for 24 hours
temperatureAfter cooling to room temperature
concentrationthe reaction was concentrated in vacuo
customthe residue was purified by silica gel chromatography
customto provide C60 as white crystals

Sources & evidence

ORD record: ord-c1d5291a2c4b4bffa9e8d0269a50c455
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145427B2

Reaction notes

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