Citric Acid → 6-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

HRID 1514708ノート

反応式

HRID 1514708 の反応式
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:18])=[N:6][CH:5]=1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>CO>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1

参加物

6

反応物 4

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 866462566-[3-(3,4-Difluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

生成物 1

HCID 667181646-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester収率 85.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

6-[3-(3,4-Difluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (3.50 g, 9.35 mmol) in methanol (125 mL) was treated with sodium borohydride (737 mg, 18.7 mmol) for 30 min at room temperature. Addition of aqueous citric acid solution (10%, 300 mL) and extraction with ethyl acetate afforded the title compound (3.0 g, 85%) as a white solid. MS: m/e=377.2 [M+H]+.

出典と根拠

ORDレコード
ord-0e745df3fff447908124d2ea63d2fbb3
出典データセット
uspto-grants-2012_07
特許番号
US08222246B2

反応ノート

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