Ammonium Chloride → tert-Butyl 3-acetylpyrrolidine-1-carboxylate

HRID 1530627Notes

Reaction equation

HRID 1530627 reaction equation
CON(C)[C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)=[O:5].[CH3:19][Mg]Cl.[NH4+].[Cl-]>C1COCC1>[C:4]([CH:6]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7]1)(=[O:5])[CH3:19]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 57419605Tert-butyl 3-[methoxy(methyl)carbamoyl]pyrrolidine-1-carboxylateHCID 178418332HCID 178418332, compound

Product 1

HCID 25257021tert-Butyl 3-acetylpyrrolidine-1-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl 3-(N-methoxy-N-methylcarbamoyl)pyrrolidine-1-carboxylate (6.30 g, 24.3 mmol) and MeMgCl (3.0 M, 40 mL) in THF (100 mL) was stirred at 0° C. for 3 h. Sat. NH4Cl was added to quench reaction. The resulting mixture was extracted with ethyl acetate (30 mL), washed with brine, dried over MgSO4, filtered, and evaporated to give tert-butyl 3-acetylpyrrolidine-1-carboxylate (3.6 g, 69% yield) as yellow oil. LCMS (ESI) m/z: 158.3 [M-56+H+].

Workup

  1. customto quench
  2. customreaction
  3. extractionThe resulting mixture was extracted with ethyl acetate (30 mL)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-df4b72f930d4447495f3fa2832316819
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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