1-Chloroethyl chloroformate → 3-(2,8-Bis(trifluoromethyl)-4-quinolinyl)-3-azetidinol

HRID 396357Notes

Reaction equation

C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][C:10]([C:13]3[C:22]4[C:17](=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:19]=[CH:20][CH:21]=4)[N:16]=[C:15]([C:27]([F:30])([F:29])[F:28])[CH:14]=3)([OH:12])[CH2:9]2)C=CC=CC=1.ClC(OC(Cl)C)=O>ClC(Cl)C>[F:30][C:27]([F:28])([F:29])[C:15]1[CH:14]=[C:13]([C:10]2([OH:12])[CH2:11][NH:8][CH2:9]2)[C:22]2[C:17](=[C:18]([C:23]([F:24])([F:25])[F:26])[CH:19]=[CH:20][CH:21]=2)[N:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 1-diphenylmethyl-3-(2,8-bis(trifluoromethyl)-4-quinolinyl)-3-azetidinol (690 mg, 1.37 mmol) in dichloroethane (20 mL), at 0° C., was added dropwise 1-chloroethyl chloroformate (0.18 mL, 1.2 eq), the mixture was stirred at 70° C. for 1 h and concentrated in vacuo. The residue was dissolved in MeOH (20 mL), stirred at room temperature for 17 h, concentrated in vacuo and the residue triturated with ether to give the title compound (351 mg, 69%) as a pale-yellow solid: mp 201° C. (dec); NMR δH (400 MHz, CDCl3) 4.44-4.45 (2H, m), 4.76-4.78 (2H, m), 7.95-7.99 (1H, m), 8.23 (1H, s), 8.38-8.42 (2H, m), 9.00 (1H, br s) and 9.47 (1H, br s); Anal. Calcd for C14H11ClF6N2O: C, 45.12; H, 2.97; N, 7.51. Found: C, 45.21: H, 3.29; N, 7.08.

Workup

concentrationconcentrated in vacuo
dissolutionThe residue was dissolved in MeOH (20 mL)
stirringstirred at room temperature for 17 h
concentrationconcentrated in vacuo
customthe residue triturated with ether

Sources & evidence

ORD record: ord-b0e5650526c347f1872667b5a3bcd991
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608085B1

Reaction notes

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