Chloride → 1-Benzyl-5-biphenyl-4-ylmethyl-5-hydroxy-pyrrolidin-2-one

HRID 882547

Reaction equation

HRID 882547 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH2:11][CH2:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Cl-].[NH4+].[CH2:18]1[CH2:22]O[CH2:20][CH2:19]1>>[CH2:1]([N:8]1[C:12]([CH2:20][C:19]2[CH:20]=[CH:19][C:18]([C:22]3[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=3)=[CH:22][CH:18]=2)([OH:13])[CH2:11][CH2:10][C:9]1=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 312ChlorideHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 952411-(Phenylmethyl)-2,5-pyrrolidinedione

Product 1

HCID 593184651-Benzyl-5-biphenyl-4-ylmethyl-5-hydroxy-pyrrolidin-2-one

Conditions

Temperature
-78 °C

Procedure

9.5 g N-Benzylsuccinimide is added to 120 ml THF and the mixture is then cooled to −78° C. A solution of 4-methylbiphenylmagnesium chloride in THF (1.3 eq) is then added. The subsequent mixture is then stirred for 2 h at −78° C. The mixture is then warmed to 10° C. and 100 ml saturated ammonium chloride solution is added. The phases are separated and the aqueous phase is extracted with toluene. The combined organic phases are washed with water then brine and then concentrated in vacuo. The crude material is crystallized from toluene to give 1-Benzyl-5-biphenyl-4-ylmethyl-5-hydroxy-pyrrolidin-2-one. 1H NMR (DMSO): 1.72 (1H), 1.91 (1H), 2.27 (2H), 2.72 (1H), 2.97 (2H), 4.40 (1H), 4.55 (1H), 7.21-7.66 (14H).

Workup

  1. temperatureThe mixture is then warmed to 10° C.
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with toluene
  4. washThe combined organic phases are washed with water
  5. concentrationbrine and then concentrated in vacuo
  6. customThe crude material is crystallized from toluene

Sources & evidence

ORD record
ord-29fc169e2f944ec0a64a3795f0f0a2ff
Source dataset
uspto-grants-2015_03
Patent number
US08993785B2

Linked notes

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