Tetrahydrofuran → 6,7-dihydro-5H-cyclopenta[c]pyridin-3-ylmethanol

HRID 1943162노트

반응식

HRID 1943162 반응식
[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[CH:4]=[C:3]([C:10](OCC)=[O:11])[N:2]=1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>O>[CH:1]1[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[CH:4]=[C:3]([CH2:10][OH:11])[N:2]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14735905Ethyl 6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 685981886,7-dihydro-5H-cyclopenta[c]pyridin-3-ylmethanol수율 57%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A solution of ethyl 6,7-dihydro-5H-cyclopenta[c]pyridine-3-carboxylate (427 mg, 2.233 mmol) in (THF) (20 ml) at −78° C. under argon was treated with LiAlH4 (1M in THF) (2.233 ml, 2.233 mmol) and allowed warm to rt. After 10 min at rt, water (1 ml), 2M aq NaOH (1 ml) and water (1 ml) were sequentially added and the mixture stirred at rt for 0.5 h. The mixture was then filtered through a short pad of Kieselguhr, eluting with THF (50 ml), organic extracts were then evaporated, chromatographed (0-20% methanol/DCM) to give product as an orange oil (189 mg, 57%).

후처리

  1. filtrationThe mixture was then filtered through a short pad of Kieselguhr
  2. washeluting with THF (50 ml), organic extracts
  3. customwere then evaporated
  4. customchromatographed (0-20% methanol/DCM)

출처 및 근거

ORD 기록
ord-f29bbf7464454e999db688c28c5c919f
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389524B2

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