Methanol → (2s)-(-)-1-(4-Indolyloxy)-3-(4-hydroxy-4-(3-trifluoromethylphenyl)piperidin-1-yl)-2-propanol ethanedioate

HRID 481592

반응식

HRID 481592 반응식
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[OH:15][C:16]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].CO>C(OCC)(=O)C>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:19]3[CH2:20][CH2:21][C:16]([OH:15])([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=4)[CH2:17][CH2:18]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

참가 물질

6

반응물 4

HCID 887MethanolHCID 971Oxalic AcidHCID 752554-[3-(Trifluoromethyl)phenyl]-4-piperidinolHCID 10943254(2s)-Glycidyl indol-4-yl ether

생성물 1

HCID 131719677(2s)-(-)-1-(4-Indolyloxy)-3-(4-hydroxy-4-(3-trifluoromethylphenyl)piperidin-1-yl)-2-propanol ethanedioate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 4-hydroxy-4-(3-trifluoromethylphenyl)piperidine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 59% overall yield. FDMS m/e=426 (M+ of free base). α[D]589 =-11.39 (c=0.56, methanol).

출처 및 근거

ORD 기록
ord-f772bd01abad40f8a0b1b0b3554d9ce6
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789402

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