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

HRID 655163

반응식

HRID 655163 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-af09548d6c284a588d17147126956e50
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071591B2

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