Sodium hydride → HCID 58348375, 화합물

HRID 2192309노트

반응식

HRID 2192309 반응식
[CH2:1]([O:3][C:4]([C:6]1([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[N:18]12CC[CH:21]([CH2:22][CH2:23]1)[C@@H:20](O)[CH2:19]2.[H-].[Na+]>C1(C)C=CC=CC=1>[N:18]12[CH2:23][CH2:22][CH:21]([CH2:20][CH2:19]1)[C@@H:1]([O:3][C:4]([C:6]1([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH2:2]2

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 914043-Quinuclidinol, (-)-HCID 583483241-Thiophen-2-yl-cycloheptanecarboxylic acid ethyl ester

생성물 1

HCID 58348375HCID 58348375, 화합물수율 86%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

1-Thiophen-2-yl-cycloheptanecarboxylic acid ethyl ester (Example 5c) (2.5 g) and (R) -quinuclidin-3-ol (2.08 g) were dissolved in toluene (350 mL) and sodium hydride (0.1 g) added under nitrogen. The mixture was heated to reflux for 20 hours after which the toluene was carefully distilled off to leave ˜100 mL which was cooled and washed with water (100 mL), dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica eluting with ethyl acetate/triethylamine (99/1) to afford the sub-titled compound (2.84 g).

후처리

  1. temperatureThe mixture was heated
  2. distillationwas carefully distilled off
  3. customto leave ˜100 mL which
  4. temperaturewas cooled
  5. washwashed with water (100 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude product was purified by column chromatography on silica eluting with ethyl acetate/triethylamine (99/1)

출처 및 근거

ORD 기록
ord-fe6cd7a005eb407dada9857f460b8b7b
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329729B2

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