Ammonium Chloride → HCID 10944755, compound

HRID 1006335Notes

Reaction equation

HRID 1006335 reaction equation
[CH3:1][Mg]Br.CON(C)[C:7]([C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:8].[Cl-].[NH4+]>O1CCCC1>[C:7]([C@@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])(=[O:8])[CH3:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10803572HCID 10803572, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 10944755HCID 10944755, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl magnesium bromide in tetrahydrofuran (1M, 36.9 ml) was added into a solution of benzyl (2S)-2-(N-methoxy-N-methylcarbamoyl)-1-pyrrolidinecarboxylate (3.6 g) in tetrahydrofuran (36 ml) under ice-cooling. After being stirred for 2 hours at the same temperature, the reaction mixture was poured into saturated aqueous ammonium chloride, and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography with a mixture of hexane and ethyl acetate (1:1) as an eluent to give benzyl (2S)-2-acetyl-1-pyrrolidinecarboxylate (0.81 g).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography with a mixture of hexane and ethyl acetate (1:1) as an eluent

Sources & evidence

ORD record
ord-266185aa268c4aa0baf22c3eccbb7088
Source dataset
uspto-grants-2004_09
Patent number
US06787543B2

Reaction notes

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