HCID 15020365、化合物 → HCID 15020366、化合物

HRID 1709859ノート

反応式

HRID 1709859 の反応式
[CH:1]1([CH:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>Cl.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.[Pt]=O>[CH:1]1([CH:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

5

反応物 1

HCID 15020365HCID 15020365、化合物

生成物 1

HCID 15020366HCID 15020366、化合物収率 50%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 82844Platinum oxide (PtO)触媒HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester溶媒

実験手順

A mixture of 4-[(cyclohexyl)(4-fluorophenyl)methyl]pyridine (10.42 g, 0.039 mole), platinum oxide (1.5 g), and 10 drops of concentrated hydrochloric acid in 200 ml of glacial acetic was subjected to hydrogenation at 80° C. and 300 p.s.i. overnight, after which NMR analysis showed 50% desired product and 50% starting material. The reaction was repeated using 5% platinum on carbon at 85° C. and 1400 p.s.i. overnight. The reaction mixture was then cooled to room temperature and filtered. Solvent was removed by rotary evaporator. The oil obtained was dissolved in chloroform and extracted with 5% sodium hydroxide and water. The chloroform layer was dried over sodium sulfate, filtered, and solvent removed to give 9.94 g of brown oil. NMR analysis showed a 75%-25% mixture of product and starting material. The 9.94 g of oil obtained was dissolved in methanol and subjected to flash chromatography on silica gel using methanol and ammonium hydroxidemethanol for elution. Fractions of similar purity were combined and solvent removed. The clear oil obtained was dried in vacuo overnight at 80° C., to give 5.86 g (59.6% yield) of title compound as a clear oil.

後処理

  1. customwas subjected to hydrogenation at 80° C.
  2. customovernight

出典と根拠

ORDレコード
ord-cb45513d4df34d82b698064cdbd9832b
出典データセット
uspto-grants-1990_08
特許番号
US04950674

反応ノート

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