Ammonium Chloride → (1RS)-1-phenyl-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl)pyrrolidin-2-yl]methanol

HRID 1077886Notes

Reaction equation

HRID 1077886 reaction equation
[CH2:1]([N:8]([CH3:22])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]=[O:21])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>C1COCC1>[C:23]1([CH:20]([C@@H:16]2[CH2:17][CH2:18][CH2:19][N:15]2[C:13](=[O:14])[CH2:12][CH2:11][C:9](=[O:10])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH3:22])[OH:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 14674666(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-alHCID 178418255HCID 178418255, compound

Product 1

HCID 15661001(1RS)-1-phenyl-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl)pyrrolidin-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-al (200 mg) in THF (5 ml) was cooled to -25° C. A solution of phenyl magnesium bromide in THF (2M, 0.49 ml) was added dropwise to the solution. The reaction solution was stirred for 30 mins, at the same temperature, and for 30 mins at 0° C. A saturated aq. solution of ammonium chloride was added to the reaction solution. The mixture was extracted with EtOAc. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (EtOAc-CH3OH) to give the title compound (45 mg) having the following physical data:

Workup

  1. waitfor 30 mins at 0° C
  2. extractionThe mixture was extracted with EtOAc
  3. washThe extract was washed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (EtOAc-CH3OH)

Sources & evidence

ORD record
ord-00b39f1054c240ac8dc919ebb966dd1f
Source dataset
uspto-grants-1996_08
Patent number
US05545657

Reaction notes

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