alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanol → HCID 15057660, compound

HRID 654040Notes

Reaction equation

C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:6]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C.[OH:25][CH:26]([CH:29]1[CH2:33][O:32][C:31]([CH3:35])([CH3:34])[O:30]1)[CH2:27][NH2:28]>C(O)C>[OH:25][CH:26]([CH:29]1[CH2:33][O:32][C:31]([CH3:35])([CH3:34])[O:30]1)[CH2:27][NH:28][C:4](=[O:3])[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([C:12]([F:13])([F:14])[F:15])[C:6]=1[O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3.42 g (10 mmol) of 2-benzyloxy-5-fluoro-3-(trifluoromethyl)-benzoic acid ethyl ester is dissolved in 10 ml of ethanol, 2.43 g (15 mmol) of 2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamine is added, the ethanol is distilled off and the remaining oil is warmed to 100° C. in a vacuum in 2 hours. The reaction mixture is then dissolved in 50 ml of ethyl acetate, shaken out twice with 10 ml of 1N hydrochloric acid each, the organic phase is dried on sodium sulfate, concentrated by evaporation and the residue is chromatographed on silica gel 60 with ethyl acetate/hexane. 2.18 g (7.18 mol) =47.68% of the theoretical yield is obtained as an amorphous solid.

Workup

distillationthe ethanol is distilled off
dissolutionThe reaction mixture is then dissolved in 50 ml of ethyl acetate
customis dried on sodium sulfate
concentrationconcentrated by evaporation
customthe residue is chromatographed on silica gel 60 with ethyl acetate/hexane
custom2.18 g (7.18 mol) =47.68% of the theoretical yield
customis obtained as an amorphous solid

Sources & evidence

ORD record: ord-638daadc894f49329ebc941c4bbfa895
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130119

Reaction notes

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