Formaldehyde → 1,2,3,9-Tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one

HRID 642920

반응식

HRID 642920 반응식
CC1N([CH2:7][CH:8]2[C:21](=[O:22])[C:12]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[N:19]([CH3:20])[C:11]=3[CH2:10][CH2:9]2)C=CN=1.CN1C2CCCC(=O)C=2C2C1=CC=CC=2.C=O.N1CCOCC1>C(O)(=O)C>[CH3:20][N:19]1[C:11]2[CH2:10][CH2:9][C:8](=[CH2:7])[C:21](=[O:22])[C:12]=2[C:13]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=2

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 4595OndansetronHCID 8083MorpholineHCID 5988759-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one2회

생성물 1

HCID 117905051,2,3,9-Tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Kim et al. (Heterocycles 1997, 45, 2041) disclose a two-step synthesis of ondansetron. In the first step of the synthesis, 1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one (compound of formula 1, Scheme 1) is reacted with a source of formaldehyde and morpholine in boiling glacial acetic acid to provide 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one (compound of formula 2, Scheme 1). In the second step of the synthesis, 1,2,3,9-tetrahydro-9-methyl-3-methylene-4H-carbazol-4-one is reacted with 2-methylimidazole in the presence of alumina (Al2O3) to provide ondansetron (See, Scheme 1).

출처 및 근거

ORD 기록
ord-ab14a4ed59114cde9f6a7f164b3efe91
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696356B2

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