4-(Hydroxymethyl)benzeneboronic acid → 1-Methylethyl 4-({[4'-(hydroxymethyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylate

HRID 423470Notes

Reaction equation

HRID 423470 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[CH:15][CH:14]=1>>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH:21]3[CH2:22][CH2:23][N:24]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]3)=[CH:17][CH:18]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 579303004-(4-Bromophenoxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 591777401-Methylethyl 4-({[4'-(hydroxymethyl)-4-biphenylyl]oxy}methyl)-1-piperidinecarboxylateYield 4.2%

Procedure

The title compound (1.6 mg, 4%) was prepared from [4-(hydroxymethyl)phenyl]boronic acid (15.2 mg, 0.1 mmol) and 1-methylethyl 4-{[(4-bromophenyl)oxy]methyl}-1-piperidinecarboxylate (Example 9, Step 2, 36 mg, 0.10 mmol) in a manner similar to Example 9, Step 3. LRMS (ESI), m/z 406 (M+Na).

Sources & evidence

ORD record
ord-7f877b7780604813b9b7e91794772754
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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