(2s)-Glycidyl indol-4-yl ether → (2S)-(+)-3-[4-(5-fluoro-3-indolyl)piperidin-1-yl]-1-(4-indolyloxy)-2-propanol

HRID 565561Notes

Reaction equation

HRID 565561 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[O:17]1[CH2:19][C@H:18]1[CH2:20][O:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][NH:26]2>CO.CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH2:19][C@H:18]([OH:17])[CH2:20][O:21][C:22]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:23]=2[CH:24]=[CH:25][NH:26]3)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 117699295-fluoro-3-(piperidin-4-yl)-1H-indole

Product 1

HCID 70216375(2S)-(+)-3-[4-(5-fluoro-3-indolyl)piperidin-1-yl]-1-(4-indolyloxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 193 from 5-fluoro-3-(piperidin-4-yl)-1H-indole (0.87 g, 4.0 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.76 g, 4.0 mmol). The product was isolated as a white foam. Yield 1.14 g (70%). mp 94-97° C. FDMS m/e=407 (M+ of free base). α[D]589=+8.36 (c=1.00, methanol/dimethylsulfoxide).

Workup

  1. customThe product was isolated as a white foam

Sources & evidence

ORD record
ord-ed7faf72cac34808be15706a54e7fabf
Source dataset
uspto-grants-2001_01
Patent number
US06172073B2

Reaction notes

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