Benzyl 4-oxo-2-phenylpiperidine-1-carboxylate → HCID 59563650, compound

HRID 1805944Notes

Reaction equation

HRID 1805944 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH:12]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[OH:17][C:14]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH:12]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 15482876Benzyl 4-oxo-2-phenylpiperidine-1-carboxylateHCID 178418255HCID 178418255, compound

Product 1

HCID 59563650HCID 59563650, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl-4-oxo-2-phenylpiperidine-1-carboxylate (1.64 g, 5.30 mmol) in THF (27 ml) was cooled to −78° C. and phenylmagnesium bromide (6.36 ml, 6.36 mmol) was added. The ice bath was removed and the solution stirred at room temperature for 2 h. Concentrate, dilute with EtOAc and wash twice with water. The organics were dried over MgSO4, concentrated, and purified on silica gel eluted using 30% EtOAc to afford 1.02 g of benzyl 4-hydroxy-2,4-diphenylpiperidine-1-carboxylate.

Workup

  1. customThe ice bath was removed
  2. concentrationConcentrate
  3. additiondilute with EtOAc
  4. washwash twice with water
  5. dry with materialThe organics were dried over MgSO4
  6. concentrationconcentrated
  7. custompurified on silica gel
  8. washeluted

Sources & evidence

ORD record
ord-518bc7ea67dc4badb6fbdb03682924e2
Source dataset
uspto-grants-2013_01
Patent number
US08354545B2

Reaction notes

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