Water → (RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

HRID 443835ノート

反応式

HRID 443835 の反応式
[C:1]([CH:4]1[NH:9][CH2:8][C:7]2[CH:10]=[CH:11][S:12][C:6]=2[CH2:5]1)(O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:2][CH2:1][CH:4]1[NH:9][CH2:8][C:7]2[CH:10]=[CH:11][S:12][C:6]=2[CH2:5]1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 12685848(RS)-6-Carboxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridineHCID 21226445Aluminium lithium hydride

生成物 1

HCID 12939919(RS)-6-hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine収率 35.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(RS)-6-Carboxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3.7 g) is added, under a nitrogen atmosphere and in small portions, to a solution of lithium aluminum hydride (1.1 g) in tetrahydrofuran (45 cc); the resulting suspension is heated under reflux for 4 hours. After cooling, water (1.35 cc), 5N aqueous sodium hydroxide solution (0.95 cc) and water (4.35 cc) are successively added dropwise. The inorganic salts formed are filtered off and washed with methylene chloride (5×20 cc). The filtrates are combined and evaporated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 60° C. The residue is dissolved in boiling acetonitrile (15 cc) and the solution is cooled and then kept at 5° C. for 20 hours. The resulting crystals are filtered off, washed with cyclohexane and dried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa). (RS)-6-Hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1.2 g), melting at 110° C., is thus obtained.

後処理

  1. temperaturethe resulting suspension is heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. customThe inorganic salts formed
  5. filtrationare filtered off
  6. washwashed with methylene chloride (5×20 cc)
  7. customevaporated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 60° C
  8. dissolutionThe residue is dissolved
  9. temperaturethe solution is cooled
  10. filtrationThe resulting crystals are filtered off
  11. washwashed with cyclohexane
  12. customdried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

出典と根拠

ORDレコード
ord-2a38a7c4c78b496f9dbde2517648b599
出典データセット
uspto-grants-1981_04
特許番号
US04261999

反応ノート

読み込み中…