Toluene → HCID 86636512、化合物

HRID 548233ノート

反応式

HRID 548233 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 86636512HCID 86636512、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-36435094306544778110076667f25c3f
出典データセット
uspto-grants-2011_05
特許番号
US07939666B2

反応ノート

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