Acetic Acid → (1S,3R)-3-(3-pyridyl)cyclopentyl acetate

HRID 655163

反応式

HRID 655163 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]2[CH2:11][CH2:10][C@@H:9]([OH:12])[CH2:8]2)[CH:2]=1.[C:13](O)(=[O:15])[CH3:14].CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.CCOC(C)=O>[C:13]([O:12][C@H:9]1[CH2:10][CH2:11][C@@H:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH2:8]1)(=[O:15])[CH3:14]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59486143(1R,3R)-3-(3-pyridyl)cyclopentanol

生成物 1

HCID 59486131(1S,3R)-3-(3-pyridyl)cyclopentyl acetate収率 100.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (1R,3R)-3-(3-pyridyl)cyclopentanol (3.47 g, 21.3 mmol) in THF (100 mL) was cooled to 4° C. and treated with acetic acid (1.34 mL, 23.4 mmol), Diisopropylazodicarboxylate (4.61 mL, 23.4 mmol) and triphenylphosphine (6.14 g, 23.4 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with EtOAc, and washed with H2O and brine. The organic layers was dried over Na2SO4. After concentration under reduced pressure, the residue was purified by column chromatography (NH, Hexane/EtOAc=6/1) to yield (1S,3R)-3-(3-pyridyl)cyclopentyl acetate (4.39 g, 100%) as colorless oil.

後処理

  1. washwashed with H2O and brine
  2. dry with materialThe organic layers was dried over Na2SO4
  3. concentrationAfter concentration under reduced pressure
  4. customthe residue was purified by column chromatography (NH, Hexane/EtOAc=6/1)

出典と根拠

ORDレコード
ord-af09548d6c284a588d17147126956e50
出典データセット
uspto-grants-2011_12
特許番号
US08071591B2

関連ノート

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