tert-Butyl 3-methyl-4-oxopiperidine-1-carboxylate → tert-Butyl 4-(3-benzyloxyphenyl)-4-hydroxy-3-methylpiperidine-1-carboxylate

HRID 537217Notes

Reaction equation

HRID 537217 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[CH2:16]([O:23][C:24]1[CH:25]=[C:26]([Mg]Br)[CH:27]=[CH:28][CH:29]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][C:24]1[CH:29]=[C:28]([C:7]2([OH:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:3][CH:2]2[CH3:1])[CH:27]=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 22644642tert-Butyl 3-methyl-4-oxopiperidine-1-carboxylateHCID 178419633HCID 178419633, compound

Product 1

HCID 86676855tert-Butyl 4-(3-benzyloxyphenyl)-4-hydroxy-3-methylpiperidine-1-carboxylateYield 44%

Procedure

This compound was prepared from tert-Butyl 3-methyl-4-oxopiperidine-1-carboxylate and 3-benzyloxyphenylmagnesium bromide as described in Step 1 of Example 6 in 44% yield.

Sources & evidence

ORD record
ord-0fbfab2e44194e98ae04264082fcc295
Source dataset
uspto-grants-2014_10
Patent number
US08859777B2

Reaction notes

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