Tert-butyl 3-oxopyrrolidine-1-carboxylate → HCID 18675808, compound

HRID 242546Notes

Reaction equation

HRID 242546 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([Mg]Br)=[CH:17][CH:16]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:18]2[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=2)([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178478191HCID 178478191, compound

Product 1

HCID 18675808HCID 18675808, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-t-butoxycarbonyl-3-pyrrolidinone (0.57 g, 3.23 mmol) in THF (10 mL) was added 4-chlorophenyl magnesium bromide (1.0 M, 5.2 mL) under the protection of argon at 0° C. The reaction was stirred at room temperature for 1 hour then quenched by the addition of saturated aqueous NH4OH (8 mL). The aqueous layer was extracted with EtOAc (50 mL×2), dried over MgSO4 and concentrated in vacuo. Chromatographic purification on silica gel (Hexane/EtOAc=3/1) provided 0.57 g 1-t-butoxycarbonyl-3-(4-chlorophenyl)-3-hydroxypyrrolidine (60%). m/z 298 (m+1)

Workup

  1. customthen quenched by the addition of saturated aqueous NH4OH (8 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (50 mL×2)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customChromatographic purification on silica gel (Hexane/EtOAc=3/1)

Sources & evidence

ORD record
ord-09ded3fd6f6147688b8563e750d9178c
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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