Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilane → 4(4-{2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic acid methylamide

HRID 395986Notes

Reaction equation

C(O)=O.[NH2:4][CH2:5][CH2:6][C:7]1[CH:23]=[CH:22][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH3:21])=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.C([Si]([O:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][CH:50]2[CH2:52][O:51]2)=[CH:44][CH:43]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>>[CH3:21][NH:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][NH:4][CH2:52][C@H:50]([OH:51])[CH2:49][O:48][C:45]3[CH:46]=[CH:47][C:42]([OH:41])=[CH:43][CH:44]=3)=[CH:23][CH:22]=2)[CH2:13][CH2:14]1)=[O:19]

Participants

Reactant 2

HCID 12045564Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilane

HCID 699873764-[4-(2-Aminoethyl)anilino]-N-methyl-1-piperidinecarboxamide formate

Product 1

HCID 102751574(4-{2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic acid methylamideYield 16.7%

Procedure

4-[4-(2-Aminoethyl)anilino]-N-methyl-1-piperidinecarboxamide formate (0.322 g, 1.0 mmol) was reacted with tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.364 g, 0.90 mmol) according to Procedure G to give the title compound (eluant: 20:1 chloroform-methanol) (0.1 g, 0.15 mmol).

Sources & evidence

ORD record: ord-e100c8f7c584437aa355e99cf7e50507
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605618B2

Reaction notes

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