(S)-(+)-4-(2,3-Epoxypropoxy)carbazole → (2S)-1-(9H-Carbazol-4-yloxy)-3-{[1-(4-methoxy-benzenesulfonyl)-piperidin-4-ylmethyl]-amino}-propan-2-ol

HRID 1634786Notes

Reaction equation

HRID 1634786 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.NCC1CCN([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=2[S:35]([NH2:38])(=[O:37])=[O:36])CC1>>[CH:9]1[C:10]2[NH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][NH:11][CH2:10][CH:18]2[CH2:6][CH2:7][N:38]([S:35]([C:28]3[CH:27]=[CH:32][C:31]([O:33][CH3:34])=[CH:30][CH:29]=3)(=[O:36])=[O:37])[CH2:16][CH2:17]2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazoleHCID 18678703HCID 18678703, compound

Product 1

HCID 10118955(2S)-1-(9H-Carbazol-4-yloxy)-3-{[1-(4-methoxy-benzenesulfonyl)-piperidin-4-ylmethyl]-amino}-propan-2-olYield 124.9%

Procedure

Prepared from 4-[(2S)-Oxiranylmethoxy]-9H-carbazole (0.125 g, 0.52 mmol) and (4-aminomethyl-1-piperidinyl) 4-methoxybenzenesulfonamide (0.255 g, 0.9 mmol) according to procedure used for Example 2 to give 0.170 g of the title compound as a white solid.

Sources & evidence

ORD record
ord-39285ee184834e81bafe3416e591040f
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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