Methanol → (2S)-(-)-1-(4-indolyloxy)-3-(3,3-diphenylpyrrolidin-1-yl)-2-propanol ethanedioate

HRID 565481

반응식

HRID 565481 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.[C:15]1([C:21]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:25][CH2:24][NH:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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:23]3[CH2:24][CH2:25][C:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:22]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

참가 물질

6

반응물 4

HCID 887MethanolHCID 971Oxalic AcidHCID 4182423,3-DiphenylpyrrolidineHCID 10943254(2s)-Glycidyl indol-4-yl ether

생성물 1

HCID 131719694(2S)-(-)-1-(4-indolyloxy)-3-(3,3-diphenylpyrrolidin-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 3,3-diphenylpyrrolidine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 68% overall yield. FDMS m/e=412 (M+ of free base). mp 193-194°. α[D]589=−9.11 (c=0.33, methanol).

출처 및 근거

ORD 기록
ord-4b1d6c5db970421ca2a169ba87c9c0ee
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172073B2

연결된 노트

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