Diboron → N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-N-(2-hydroxyethyl)-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

HRID 1451464Notes

Reaction equation

HRID 1451464 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([N:15]([CH2:28][CH2:29][OH:30])[CH2:16][CH:17]([OH:27])[C:18]2[N:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[S:21][CH:22]=2)[CH3:14])=[CH:8][CH:7]=1)(O)=[O:2].B#B.C(OCC)(=O)C.CO>O1CCCC1>[OH:2][CH2:1][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH:13]([N:15]([CH2:28][CH2:29][OH:30])[CH2:16][CH:17]([OH:27])[C:18]2[N:19]=[C:20]([C:23]([F:25])([F:24])[F:26])[S:21][CH:22]=2)[CH3:14])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6328200DiboronHCID 19974169N-[2-(4-Carboxymethoxyphenyl)-1-methylethyl]-N-(2-hydroxyethyl)-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamineHCID 21584119Ethylacetate methanol

Product 1

HCID 19974284N-[2-(4-(2-Hydroxyethoxy)-phenyl)-1-methylethyl]-N-(2-hydroxyethyl)-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prepared by analogy to Example 71 by reaction of N-[2-(4-carboxymethoxyphenyl)-1-methylethyl]-N-(2-hydroxyethyl)-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine in tetrahydrofuran with diborane in tetrahydrofuran and purification of the base on a silica gel column using an ethyl acetate/methanol=20:1 as eluant.

Sources & evidence

ORD record
ord-9e866af27e3144b5a1a7198a40380f74
Source dataset
uspto-grants-1997_02
Patent number
US05604225

Reaction notes

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