Toluene → HCID 86636512, 화합물

HRID 548233노트

반응식

HRID 548233 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH:12]1[C:24](O)=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH:12]1[CH:24]=[O:25])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 190319922-[(benzyloxy)carbonyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylic acid

생성물 1

HCID 86636512HCID 86636512, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1,3,4,9-tetrahydro-beta-carboline-1,2-dicarboxylic acid 2-benzyl ester (3.7 mg, 9.4 mmol) in THF (100 ml) under N2 was cooled to −78° C. 1.5M DIBAL in toluene solution (31.2 ml, 47 mmol) was added over 2 hours. After stirring for 4 hours the reaction mixture was quenched with methanol and water, extracted into EtOAc and washed with dilute aqueous HCl. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. LCMS purity 50%, m/z 335 [M++H]+ The material was used in the next stage without further purification.

후처리

  1. customwas quenched with methanol and water
  2. extractionextracted into EtOAc
  3. washwashed with dilute aqueous HCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customLCMS purity 50%, m/z 335 [M++H]+ The material was used in the next stage without further purification

출처 및 근거

ORD 기록
ord-36435094306544778110076667f25c3f
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939666B2

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