HCID 67329422、化合物 → HCID 53373132、化合物

HRID 1846161ノート

反応式

HRID 1846161 の反応式
C([O:8][C:9]1[C:10]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28]COC)=[N:11][C:12]([O:16][CH3:17])=[CH:13][C:14]=1[CH3:15])C1C=CC=CC=1>CO.Cl.[OH-].[OH-].[Pd+2]>[OH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][C:10]1[C:9]([OH:8])=[C:14]([CH3:15])[CH:13]=[C:12]([O:16][CH3:17])[N:11]=1

参加物

5

反応物 1

HCID 67329422HCID 67329422、化合物

生成物 1

HCID 53373132HCID 53373132、化合物

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 9942167Palladium hydroxide触媒HCID 887Methanol溶媒

実験手順

To a stirred solution containing 18 mg (0.04 mmol) of 3-(benzyloxy)-6-methoxy-2-(10-(methoxymethoxy)decyl)-4-methylpyridine in 3 mL of methanol were added two drops of concentrated HCl. The reaction mixture was stirred at reflux for 16 h. To the mixture were added 3 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/N). The reaction mixture was stirred at room temperature under hydrogen atmosphere for 15 min. The reaction mixture was filtered through celite and the filtrate was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (5×1 cm). Elution with 3:1 hexanes-ethyl acetate afforded the expected product as white solid: yield 8 mg (67%); mp: 80-81° C.; silica gel TLC Rf 0.50 (3:1 hexanes-ethyl acetate); 1H NMR (methanol-d4) δ 1.27 (br s, 12H), 1.49 (br s, 2H), 1.64 (br s, 2H), 2.41 (br s, 3H), 2.81 (br s, 2H), 3.51 (br s, 3H), 4.02 (br s, 1H) and 7.05 (br s, 1H); 13C NMR (methanol-d4) δ 16.59, 25.51, 28.13, 28.57, 28.92, 28.97, 29.09, 29.14, 29.24, 32.22, 56.39, 61.56, 107.60, 142.26, 145.27, 148.68 and 155.10; mass spectrum (APCI+), m/z 296.2220 (M+H) (C17H30NO3 requires 296.2226).

後処理

  1. temperatureat reflux for 16 h
  2. stirringThe reaction mixture was stirred at room temperature under hydrogen atmosphere for 15 min
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated under diminished pressure
  5. customThe residue was purified by chromatography on a silica gel column (5×1 cm)
  6. washElution with 3:1 hexanes-ethyl acetate

出典と根拠

ORDレコード
ord-1a24b973ea65410d8405d956195ab779
出典データセット
uspto-grants-2015_02
特許番号
US08952025B2

反応ノート

読み込み中…