Hydrochloric Acid → 3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid 4-isopropyl-benzyl ester

HRID 1269508

反応式

HRID 1269508 の反応式
[CH:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:12](N1C=CN=C1)(N1C=CN=C1)=[O:13].[CH2:24]([O:31][C:32](=[O:49])[C:33]([CH3:48])([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH:42]2[CH2:47][CH2:46][CH2:45][NH:44][CH2:43]2)[CH:37]=1)[CH3:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>C1(C)C=CC=CC=1.O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:12]([N:44]2[CH2:45][CH2:46][CH2:47][CH:42]([C:38]3[CH:39]=[CH:40][CH:41]=[C:36]([O:35][C:33]([C:32]([O:31][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:49])([CH3:34])[CH3:48])[CH:37]=3)[CH2:43]2)=[O:13])=[CH:10][CH:11]=1)([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 325CuminolHCID 682631,1'-CarbonyldiimidazoleHCID 688839562-Methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid benzyl ester

生成物 1

HCID 688826363-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid 4-isopropyl-benzyl ester収率 56.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

To a solution of 4-isopropylbenzyl alcohol (0.86 g, 5.75 mmol) in 10 mL toluene was added 1,1′-carbonyldiimidazole (0.87 g, 5.40 mmol). This solution was stirred 18 h at ambient temperature. 2-methyl-2-(3-piperidin-3-yl-phenoxy)-propionic acid benzyl ester (Preparation 2, Method C; 1.27 g, 3.59 mmol) was added in 5 mL toluene and the resultant solution was stirred 18 h at ambient temperature. The reaction was diluted with water (200 mL), acidified with 1N aqueous hydrochloric acid and extracted with diethyl ether (2×150 mL). The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was flash chromatographed with 10% ethyl acetate/hexanes to yield 1.07 g (56%) of the desired 3-[3-(1-Benzyloxycarbonyl-1-methyl-ethoxy)-phenyl]-piperidine-1-carboxylic acid 4-isopropyl-benzyl ester as a clear oil.

後処理

  1. extractionextracted with diethyl ether (2×150 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 10% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-814fb5b92bb949e690100f212315ae24
出典データセット
uspto-grants-2007_04
特許番号
US07199243B2

関連ノート

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