(2s)-Glycidyl indol-4-yl ether → (2S)-(+)-3-[4-(6-fluoro-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)-2-propanol

HRID 1901032Notes

Reaction equation

HRID 1901032 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=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>CS(C)=O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][N:14]([CH2:19][C@H:18]([OH:17])[CH2:20][O:21][C:22]4[CH:30]=[CH:29][CH:28]=[C:27]5[C:23]=4[CH:24]=[CH:25][NH:26]5)[CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 110530726-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 57064041(2S)-(+)-3-[4-(6-fluoro-3-indolyl)-1,2,3,6-tetrahydropyridin-1-yl]-1-(4-indolyloxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 193 from 6-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (1.00 g, 4.63 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.88 g, 4.6 mmol). The resulting free base was obtained as a yellow foam. Yield 1.2 g (64%). mp 95°-100° C. FDMS m/e=405 (M+ of free base). α[D]589 =5.15 (c=1.01, dimethylsulfoxide).

Workup

  1. customThe resulting free base was obtained as a yellow foam

Sources & evidence

ORD record
ord-5c667421e6054f689eef703b00dfca19
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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