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

HRID 883733노트

반응식

HRID 883733 반응식
[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]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 24875831HCID 24875831, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e547fbee14694f29af3203047de8e59c
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236969B2

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