tert-Butyl isocyanate → HCID 67937983, 화합물

HRID 364127노트

반응식

HRID 364127 반응식
[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]

참가 물질

7

반응물 3

HCID 62412tert-Butyl isocyanateHCID 20154007HCID 20154007, 화합물HCID 178418339Butyllithium

생성물 1

HCID 67937983HCID 67937983, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-61c4f0de62aa4cfb88183e97abf41776
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04604397

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