tert-Butyl 4-oxopiperidine-1-carboxylate → N-t-Butoxycarbonyl-4-(3-methylphenyl)-4-hydroxy piperidine

HRID 443215Notes

Reaction equation

HRID 443215 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](=[O:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH2:19][C:20]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[CH:7]=2)([OH:23])[CH2:21][CH2:22]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178425413HCID 178425413, compound

Product 1

HCID 21193300N-t-Butoxycarbonyl-4-(3-methylphenyl)-4-hydroxy piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-methylphenyl magnesium bromide (58 ml of a 1M solution in THF, 58.0 mmol) at 0° C. was added a solution of N-t-butoxycarbonyl piperidin-4-one (10.0 g, 53mmol) in THF (30 ml) dropwise over 20 min, and the reaction stirred under argon for a further 30 min. The reaction was quenched by addition of sat NH4Cl solution (100 ml), and diluted with EtOAc. The organic extracts were dried, (MgSO4) and the solvent evaporated in vacuo to afford the title compound of sufficient purity to be used in the next step.

Workup

  1. customThe reaction was quenched by addition of sat NH4Cl solution (100 ml)
  2. additiondiluted with EtOAc
  3. customThe organic extracts were dried
  4. custom(MgSO4) and the solvent evaporated in vacuo

Sources & evidence

ORD record
ord-199e1ccf53034887a75bfc106a82106f
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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