Tetrabutylammonium Fluoride → Methyl 7-{(1R,2S,3R,5S)-5-(acetyloxy)-2-(hydroxymethyl)-3-[(oxan-2-yl)oxy]cyclopentyl}heptanoate

HRID 883733Notes

Reaction equation

HRID 883733 reaction equation
[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]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 24875831HCID 24875831, compound

Product 1

HCID 22789843Methyl 7-{(1R,2S,3R,5S)-5-(acetyloxy)-2-(hydroxymethyl)-3-[(oxan-2-yl)oxy]cyclopentyl}heptanoateYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e547fbee14694f29af3203047de8e59c
Source dataset
uspto-grants-2012_08
Patent number
US08236969B2

Reaction notes

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