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

HRID 1281559Notes

Reaction equation

HRID 1281559 reaction equation
C(O)=O.[NH2:4][CH2:5][CH2:6][C:7]1[CH:32]=[CH:31][C:10]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([N:20]3[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]3)=[O:19])[CH2:14][CH2:13]2)=[CH:9][CH:8]=1.C([Si]([O:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][CH2:58][CH:59]2[CH2:61][O:60]2)=[CH:53][CH:52]=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C)(C)C>C(Cl)(Cl)Cl.CO>[CH2:29]([O:28][C:26]([CH:23]1[CH2:22][CH2:21][N:20]([C:18]([N:15]2[CH2:16][CH2:17][CH:12]([NH:11][C:10]3[CH:31]=[CH:32][C:7]([CH2:6][CH2:5][NH:4][CH2:61][C@H:59]([OH:60])[CH2:58][O:57][C:54]4[CH:55]=[CH:56][C:51]([OH:50])=[CH:52][CH:53]=4)=[CH:8][CH:9]=3)[CH2:13][CH2:14]2)=[O:19])[CH2:25][CH2:24]1)=[O:27])[CH3:30]

Participants

4

Reactant 2

HCID 12045564Tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenylsilaneHCID 69986986HCID 69986986, compound

Product 1

HCID 101445481-[4-(4-{2-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-phenylamino)-piperidine-1-carbonyl]-piperidine-4-carboxylic Acid Ethyl EsterYield 42.4%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Ethyl 1-({4-[4-(2-aminoethyl)anilino]-1-piperidinyl}carbonyl)-4-piperidinecarboxylate formate (0.312 g, 0.696 mmol) was reacted with tert-butyl-(4-oxiranylmethoxy-phenoxy)-diphenyl-silane (0.20 g, 0.495 mmol) according to Procedure G (eluant: 20:1 chloroform-methanol) to give the title compound (0.17 g, 0.21 mmol).

Sources & evidence

ORD record
ord-00c04176b64e49199de66193404a206a
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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