Boron trifluoride etherate → HCID 86701300, compound

HRID 1627035Notes

Reaction equation

[CH2:1]([O:8][C@H:9]([C@@H:12]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:13][OH:14])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N@:23]1([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:25][CH:24]1[C:26]([O:28][CH3:29])=[O:27].B(F)(F)F.O(CC)CC>C(Cl)Cl>[CH2:33]([O:32][C:30]([NH:23][C@@H:24]([CH2:25][O:14][CH2:13][C@H:12]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C@@H:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][OH:11])[C:26]([O:28][CH3:29])=[O:27])=[O:31])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (2S,3S)-2,3-bis(benzyloxy)butane-1,4-diol (283 mg, 0.935 mmol), prepared as disclosed in Journal of Organic Chemistry 1991, 56(3), 1321-1322, and (S)-1-benzyl 2-methyl aziridine-1,2-dicarboxylate (110 mg, 0.468 mmol) in CH2Cl2 (1.5 mL) at −78° C. was added BF3—OEt2 (10 μL, 0.081 mmol), and the reaction mixture was stirred at −78° C. for 1 h, slowly warmed to 0° C., and then stirred at 0° C. for 3 h. The reaction mixture was directly purified by flash chromatography (SiO2) to afford the title compound as a colorless oil (208 mg, 83%): 1H NMR (400 MHz, CDCl3) δ 7.45-7.20 (m, 16H), 5.70 (d, J=8.5 Hz, 1H), 4.70-4.54 (m, 6H), 4.53-4.46 (m, 1H), 3.93 (dd, J=9.5, 3.2 Hz, 1H), 3.80-3.53 (m, 9H), 2.09-1.96 (m, 1H); 13C NMR (101 MHz, CDCl3) δ 170.72, 156.04, 138.16, 138.08, 136.24, 128.54, 128.49, 128.47, 128.20, 128.13, 127.99, 127.91, 127.89, 127.86, 79.03, 78.10, 73.09, 72.88, 71.40, 71.08, 67.08, 61.40, 54.46, 52.60; ESIMS m/z 538.4 ([M+H]+).

Workup

temperatureslowly warmed to 0° C.
stirringstirred at 0° C. for 3 h
customThe reaction mixture was directly purified by flash chromatography (SiO2)

Sources & evidence

ORD record: ord-180198bf0f434a9482adb66a5e1722ed
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785479B2

Reaction notes

Loading…