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

HRID 535031Notes

Reaction equation

HRID 535031 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-carboxylateYield 49.24%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1 g, 5.40 mmol) in ether (20 ml) was added dropwise phenylmagnesium bromide (10.3 mL, 3.0 M in ether, 6.21 mmol) at rt under nitrogen. The reaction was heated to reflux for 15 min, then cooled to rt, poured into sat. NH4Cl, extracted with ether (3x). The combined organic layers were dried over Na2SO4, concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (700 mg, 49.24%). LCMS (M+H) 264.160.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 15 min
  3. extractionextracted with ether (3x)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-aa1e926f351147029ef82015f2ff55da
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

Loading…