HCID 59163141, compound → tert-Butyl (3S)-3-acetylpyrrolidine-1-carboxylate

HRID 57621Notes

Reaction equation

HRID 57621 reaction equation
CON(C)[C:4]([C@H: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]Br>C1COCC1>[C:4]([C@H: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

4

Reactant 2

HCID 59163141HCID 59163141, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68071565tert-Butyl (3S)-3-acetylpyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate in THF (18 mL) was added methylmagnesium bromide (in ether, 3 M, 2.7 mL) at 0° C. The mixture was stirred at 0° C. for 2 hours, then quenched with saturated aqueous NH4Cl, and extracted with Et2O. The combined extracts were washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated to give the tile compound for the next step.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with Et2O
  3. washThe combined extracts were washed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the tile compound for the next step

Sources & evidence

ORD record
ord-cf7fdb567c864b6a9533f641a5ca7db8
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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