Bromocresol Green → (3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 361563

반응식

HRID 361563 반응식
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[C:15](=[O:16])[CH:14]3[CH2:17][CH2:18][CH2:19][C:13]3=[N:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[CH:6][CH:5]=1)([O-:3])=[O:2].CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.C([BH3-])#N.[Na+].Cl.CO>CO.O.O1CCCC1>[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[C:15](=[O:16])[C@H:14]3[CH2:17][CH2:18][CH2:19][C@H:13]3[NH:12][C:11]3[CH:20]=[CH:21][CH:22]=[CH:23][C:10]2=3)=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

8

반응물 4

HCID 6451Bromocresol GreenHCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanolHCID 701129649-(4-Nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

생성물 1

HCID 54563031(3aR*,10aS*)-9-(4-Nitrobenzyl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one수율 70.1%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 9-(4-nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta(e][1,4]diazepin-10(1H)-one (10.2 g, 30 mmol) and bromocresol green in a mixture of methanol (100 mL)-tetrahydrofuran (THF) (30 mL) was added sodium cyanoborohydride (2.08 g, 33 mmol). To this mixture, 10% hydrogen chloride/methanol was slowly added dropwise at the same temperature until the color of the reaction mixture had ceased to change. This reaction mixture was diluted with water and extracted with 3 portions of ethyl acetate. The pooled organic layer was washed serially with water and saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1) and crystallized from ethyl acetate-diethyl ether to provide 7.09 g (yield 70%) of the title compound. m.p. 154°-155° C.

후처리

  1. extractionextracted with 3 portions of ethyl acetate
  2. washThe pooled organic layer was washed serially with water and saturated aqueous NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate=2:1)
  7. customcrystallized from ethyl acetate-diethyl ether

출처 및 근거

ORD 기록
ord-4d7e3e52a14943f7a283dc3c2c400228
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866567

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