Ammonia → MRZ-9547

HRID 1048834Notes

Reaction equation

HRID 1048834 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[CH2:11][C@@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][C:8]1=[O:18])=O)C.[NH3:19]>CO>[C:4]([CH2:6][N:7]1[CH2:11][C@@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][C:8]1=[O:18])(=[O:3])[NH2:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59163858HCID 59163858, compound

Product 1

HCID 781883MRZ-9547Yield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solution of N-ethoxycarbonylmethyl-4(R)-phenyl-2-pyrrolidinone (3) (250 mg, 1.01 mM) in methanol (30 ml) saturated by stream of gaseous ammonia for 5 hours. Reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography with ethylacetate-hexane mixture 1:1 silicagel giving N-carbamoylmethyl-4(R)-phenyl-2-pyrrolidinone (4a) (187 mg, 85%). M.p. 107.5-108° C. [α]D20=+8.5° (c=3, MeOH). 1H NMR (CDCl3), δ: 2.61 (1H, d, d, 3-CH2); 2.87 (1H, d, d, 3-CH2); 3.54 (1H, t, 5-CH2); 3.66 (1H, quintet, 4-CH); 3.89 (1H, t, 5-CH2); 4.00 (2H, s, NCH2CO); 5.68 and 6.21 (1H and 1H, br.s and br.s, NH2); 7.20-7.40 (5H, m, C6H5).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue was purified by column chromatography with ethylacetate-hexane mixture 1:1 silicagel

Sources & evidence

ORD record
ord-a5f85dd532a748ccb68c9e53c234a3a0
Source dataset
uspto-grants-2016_07
Patent number
US09382203B2

Reaction notes

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