Ethyl Acetate → HCID 69497936, compound

HRID 460637

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH3:17][C:18]([C:20]1[O:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[C:21]=1[CH3:29])=[O:19].[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].C([O:41][CH2:42][CH3:43])(=O)C>>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[CH3:17][C:18]([C:20]1[O:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([O:34][CH2:33][C@@H:42]([OH:41])[CH2:43][N:14]3[CH2:15][CH2:16][CH:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)[CH2:12][CH2:13]3)[C:22]=2[C:21]=1[CH3:29])=[O:19]

Participants

Reactant 4

HCID 8857Ethyl Acetate

HCID 444266Maleic Acid

HCID 2507689Ethanone, 1-(3-methyl-2-benzofuranyl)-

HCID 220292644-(Naphthalen-2-yl)piperidine

Product 1

HCID 69497936HCID 69497936, compound

Procedure

By the reactions in the same manner as in Example 3 using (S)-4-glycidyloxy-3-methylbenzo(b)furan-2-yl methyl ketone (0.60 g) obtained in Starting Material Synthesis Example 72 and 4-(naphthalen-2-yl)piperidine (0.51 g), (S)-4-(2-hydroxy-3-(4-naphthalen-2-yl)piperidino)propyloxy)-3-methylbenzo(b)furan-2-yl methyl ketone (1.1 g) was obtained as a brown oil. This was dissolved in ethyl acetate and maleic acid (0.25 g) was added. The precipitated crystals were recrystallized from a mixed solvent of isopropanol-ethyl acetate to give the title compound (0.82 g) as pale-yellow crystals, melting point 163–164° C.

Workup

customwas obtained as a brown oil
customThe precipitated crystals were recrystallized from a mixed solvent of isopropanol-ethyl acetate

Sources & evidence

ORD record: ord-888c58cf896f4edeb77d3319628a93b9
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196199B2

Linked notes

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