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

HRID 1943162ノート

反応式

HRID 1943162 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-f29bbf7464454e999db688c28c5c919f
出典データセット
uspto-grants-2013_03
特許番号
US08389524B2

反応ノート

読み込み中…