HCID 67329422, 화합물 → HCID 53373132, 화합물

HRID 1846161노트

반응식

HRID 1846161 반응식
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

참가 물질

5

반응물 1

HCID 67329422HCID 67329422, 화합물

생성물 1

HCID 53373132HCID 53373132, 화합물

시약·촉매·용매 3

HCID 313Hydrochloric Acid촉매HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1a24b973ea65410d8405d956195ab779
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952025B2

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