(S)-5-Oxopyrrolidine-2-carboxamide → (S)-5-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

HRID 1668420Notes

Reaction equation

HRID 1668420 reaction equation
C(O[C:9]([N:11]1[C@H:15]([C:16](=[O:26])[NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13][C:12]1=[O:27])=O)C1C=CC=CC=1.N1C(=O)CC[C@H]1C(N)=O.[Li+].[B-](CC)(CC)CC>C1COCC1>[CH2:18]([NH:17][C:16]([C@@H:15]1[CH2:14][CH2:13][CH:12]([OH:27])[N:11]1[CH3:9])=[O:26])[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 444439(S)-5-Oxopyrrolidine-2-carboxamideHCID 23712863Lithium triethylborohydrideHCID 57612752(S)-2-Oxo-5-phenethylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 66995346(S)-5-Hydroxy-1-methyl-pyrrolidine-2-carboxylic acid phenethyl-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A THF solution of 11A pyroglutamide (3.9 g, 11 mmol) is chilled to −78° C. After 15 minutes, 1 M super-hydride solution (13 mL, 13 mmol) is slowly added. After 1 hour, it is carefully quenched with saturated bicarb and added 4 mL 30% hydrogen peroxide and concentrated to half volume and reconstituted with ethyl acetate, then washed with saturated bicarb and brine and dried over anhydrous sodium sulfate, filtered and concentrated to a clear oil. LCMS characterization ES+369.1 (m+1).

Workup

  1. waitAfter 1 hour
  2. customit is carefully quenched with saturated bicarb
  3. additionadded 4 mL 30% hydrogen peroxide
  4. concentrationconcentrated to half volume
  5. washwashed with saturated bicarb and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a clear oil

Sources & evidence

ORD record
ord-6a33df16ef434bfbb2e051b70bf35eb1
Source dataset
uspto-grants-2011_08
Patent number
US07989441B2

Reaction notes

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