tert-Butyl isocyanate → HCID 67937983、化合物

HRID 364127ノート

反応式

HRID 364127 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]>O1CCCC1.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 tetrahydrofuran is added 3.4 ml of 1.5M butyllithium 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 with 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, m.p. 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-61c4f0de62aa4cfb88183e97abf41776
出典データセット
uspto-grants-1986_08
特許番号
US04604397

反応ノート

読み込み中…