(2s)-Glycidyl indol-4-yl ether → (2S)-(-)-1-(4-indolyloxy)-3-[4-hydroxy-4-(6-benzyloxynaphth-2-yl)piperidine-1-yl]-2-propanol

HRID 1416209Notes

Reaction equation

HRID 1416209 reaction equation
[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:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:28]=3)[CH:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>>[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:31]=[CH:30][C:29]5[C:24](=[CH:25][CH:26]=[C:27]([O:32][CH2:33][C:34]6[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=6)[CH:28]=5)[CH:23]=4)[CH2:17][CH2:18]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Participants

3

Reactant 2

HCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 542319294-Hydroxy-4-(6-benzyloxynaphth-2-yl)piperidine

Product 1

HCID 67573992(2S)-(-)-1-(4-indolyloxy)-3-[4-hydroxy-4-(6-benzyloxynaphth-2-yl)piperidine-1-yl]-2-propanolYield 83%

Procedure

Beginning with 0.170 gm (0.90 mmol) (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 0.300 gm (0.90 mMol) 4-hydroxy-4-(6-benzyloxynaphth-2-yl)piperidine, 0.388 gm (83%) of the title compound were recovered as a white solid by the procedure described in Example 9.

Sources & evidence

ORD record
ord-19f80b60d40b4dd8aa3d11701a3ac5a2
Source dataset
uspto-grants-1999_06
Patent number
US05912256

Reaction notes

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