Tetrabutylammonium Fluoride → Methyl 7-((1R,2S,3R,5S)-5-acetoxy-2-(hydroxymethyl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)heptanoate

HRID 883733ノート

反応式

HRID 883733 の反応式
[C:1]([O:4][C@@H:5]1[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C@@H:8]([CH2:20][O:21][Si](C(C)(C)C)(C)C)[C@H:7]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[CH2:6]1)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:4][C@@H:5]1[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C@@H:8]([CH2:20][OH:21])[C@H:7]([O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)[CH2:6]1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 24875831HCID 24875831、化合物

生成物 1

HCID 22789843Methyl 7-((1R,2S,3R,5S)-5-acetoxy-2-(hydroxymethyl)-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)heptanoate収率 98.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of methyl 7-[(1R,2S,3R,5S)-5-acetoxy-2-(t-butyldimethylsilyloxymethyl)-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanate (27) (118.7 g, 230.6 mmol) in tetrahydrofuran (450 ml) was cooled on ice. A solution of 1M-tetra butyl ammonium fluoride (in THF, 277 ml, 277 mmol) was added drop wise thereto and the mixture was stirred at room temperature for 20.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (Fuji Silysia BW-300: 2000 g; ethyl acetate:hexane =1:1). The fractions containing impurities were re-purified by silica gel column chromatography (Fuji Silysia BW-300: 520 g; ethyl acetate:hexane =1:1) to give methyl 7-[(1R,2S,3R,5S)-5-acetoxy-2-hydroxymethyl-3-(2-tetrahydropyranyloxy)cyclopentyl]heptanate (28) (90.64 g, 226.3 mmol, 98.1%) as colorless oil.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (Fuji Silysia BW-300: 2000 g; ethyl acetate:hexane =1:1)
  3. additionThe fractions containing impurities
  4. customwere re-purified by silica gel column chromatography (Fuji Silysia BW-300: 520 g; ethyl acetate:hexane =1:1)

出典と根拠

ORDレコード
ord-e547fbee14694f29af3203047de8e59c
出典データセット
uspto-grants-2012_08
特許番号
US08236969B2

反応ノート

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