tert-Butyl isocyanate → HCID 67937983、化合物

HRID 2414176ノート

反応式

HRID 2414176 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:17][CH2:16][CH:10]3[N:11]([CH3:15])[CH2:12][CH2:13][CH:14]=[C:9]3[C:7]=2[CH:8]=1.C([Li])CCC.[C:23]([N:27]=[C:28]=[O:29])([CH3:26])([CH3:25])[CH3:24]>C1COCC1.CCCCCC.O>[C:23]([NH:27][C:28]([C@H:13]1[CH2:12][N:11]([CH3:15])[C@@H:10]2[CH2:16][O:17][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=3[C:9]2=[CH:14]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

参加物

7

反応物 3

HCID 62412tert-Butyl isocyanateHCID 20154007HCID 20154007、化合物HCID 178418339Butyllithium

生成物 1

HCID 67937983HCID 67937983、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

To a well stirred solution of 1.16 g of 9-methoxy-4-methyl-2,3,4a,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridine in 15 ml of THF is added 3.4 ml of 1.5M butyl lithium in hexane at 0°. After 5 minutes at 0°, the reaction mixture is cooled to -70° and 0.6 ml of t-butyl isocyanate is added. After warming to room temperature the reaction mixture is diluted with water and the products extracted with ether. After drying over magnesium sulfate, the solvent is removed in vacuo and the residue is crystallized from ether/hexane to yield cis-2-(N-t-butylcarbamoyl)-9-methoxy-4-methyl-2,3,4a,5,-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridine, which is converted wiht ethanolic hydrogen chloride to cis-2-(N-t-butylcarbamoyl)-9-methoxy-4-methyl-2,3,4a,5-tetrahydro-4H-[1]-benzopyrano[3,4-b]pyridine hydrochloride, melting point 188°-189° (from ethanol/ether).

後処理

  1. temperaturethe reaction mixture is cooled to -70°
  2. extractionthe products extracted with ether
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe solvent is removed in vacuo
  5. customthe residue is crystallized from ether/hexane

出典と根拠

ORDレコード
ord-71bada114eb5410fa83301e6faeb52d2
出典データセット
uspto-grants-1988_01
特許番号
US04721787

反応ノート

読み込み中…