Ammonium Chloride → Tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate

HRID 504405Notes

Reaction equation

HRID 504405 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[C:14]1([Mg]Br)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[NH4+].[Cl-]>CCOCC>[OH:1][C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418255HCID 178418255, compound

Product 1

HCID 66662569Tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1.0 g, 0.0054 mol) in ether (20.000 mL, 0.19050 mol) was added dropwise a solution of phenylmagnesium bromide (1.12 g, 0.00621 mol) in ether (10.3 mL) at rt under N2. After the addition was complete, the reaction mixture was heated to reflux for 15 min. and then cooled to rt. The reaction mixture was poured into saturated NH4Cl and extracted with ether (3×). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The product was purified by Combiflash eluting with 0-40% EtOAc-hexanes. The product was confirmed by 1H NMR and LC/MS: m/z 286.0 (M+Na)+.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 15 min.
  4. extractionextracted with ether (3×)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by Combiflash
  8. washeluting with 0-40% EtOAc-hexanes

Sources & evidence

ORD record
ord-694a88b1a9d24fb58692e8bef1e1df32
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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