Sodium borohydride → Tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

HRID 2036690노트

반응식

HRID 2036690 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[C:16]4[CH2:22][CH:23]5[NH:27][CH:26]([C:15]=4[C:14]=3[C:13]=2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25][CH2:24]5)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CO.[Co](Cl)Cl>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([S:9]([C:12]2[CH:20]=[CH:19][C:18]3[N:17]([CH3:21])[C:16]4[CH2:22][CH:23]5[NH:27][CH:26]([C:15]=4[C:14]=3[C:13]=2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25][CH2:24]5)(=[O:11])=[O:10])=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 67085455Tert-butyl 2-(4-cyanophenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate

생성물 1

HCID 67085186Tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate수율 43.7%

시약·촉매·용매 2

HCID 24288Cobalt(II) chloride촉매HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

A mixture of the product of Example 30, step A (92 mg, 0.19 mmol) and cobalt(II) chloride (25 mg, 0.19 mmol) in anhydrous methanol (1.5 mL), cooled to 0° C. was treated with sodium borohydride (22 mg, 0.58 mmol). The reaction mixture was stirred at 0° C. for 2 h then quenched with water and filtered through a celite bed. The filtrate was concentrated in vacuo and extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide) to give tert-butyl 2-(4-aminomethylphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole-carboxylate (40 mg, 43%) as a light-yellow solid: ESI MS m/z 382 [M+H]+

후처리

  1. customthen quenched with water
  2. filtrationfiltered through a celite bed
  3. concentrationThe filtrate was concentrated in vacuo
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (SiO2, 80:18:2 chloroform/methanol/ammonium hydroxide)

출처 및 근거

ORD 기록
ord-36983bd1d21a4deeae86bb0ba91ec509
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575186B2

반응 노트

불러오는 중…