Tributylphosphine → 4-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

HRID 658233

反応式

HRID 658233 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][OH:20])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:6]1)=[O:4].[Cl:28][C:29]1[C:34](O)=[C:33]([Cl:36])[CH:32]=[C:31]([CH3:37])[CH:30]=1.P(CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][C:34]3[C:29]([Cl:28])=[CH:30][C:31]([CH3:37])=[CH:32][C:33]=3[Cl:36])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:6]1)=[O:4]

参加物

5

反応物 3

HCID 13831TributylphosphineHCID 170772,6-Dichloro-4-methylphenolHCID 684262404-[4-(2-Hydroxyethoxy)phenyl]piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester

生成物 1

HCID 671487224-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester収率 90.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
50 °C

実験手順

A mixture of compound 4-[4-(2-Hydroxyethoxy)phenyl]piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (5.50 g, 15 mmol), 2,6-dichloro-p-cresol (3.08 g, 18 mmol), azodicarboxylic dipiperidine (7.31 g, 29 mmol) and PBu3 (14 mL, 58 mmol) in toluene (150 mL) was heated to 50° C. for 16 h. The mixture was allowed to cool to rt, filtered, and the precipitate was washed with toluene. The filtrate was diluted with EtOAc, and washed with water (2×) and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 0:1→1:9→2:8) yielded the compound as a colorless oil (7.3 g, 90%). LC-MS: tR=1.18 min, ES+=538.34.

後処理

  1. temperatureto cool to rt
  2. filtrationfiltered
  3. washthe precipitate was washed with toluene
  4. additionThe filtrate was diluted with EtOAc
  5. washwashed with water (2×) and brine
  6. dry with materiallayer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvents were removed under reduced pressure
  9. customPurification of the crude by FC (EtOAc/heptane 0:1→1:9→2:8)

出典と根拠

ORDレコード
ord-0601ea16034042da90eac4477089c26d
出典データセット
uspto-grants-2011_12
特許番号
US08076359B2

関連ノート

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