(3S)-5-Oxo-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxylic acid → HCID 13772856, compound

HRID 2382983Notes

Reaction equation

HRID 2382983 reaction equation
[O:1]=[C:2]1[N:6]([C@H:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:8])[CH2:5][C@@H:4]([C:15]([OH:17])=[O:16])[CH2:3]1.[CH3:18]O.Cl>>[O:1]=[C:2]1[N:6]([C@H:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:8])[CH2:5][C@@H:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:3]1

Participants

3

Reactant 2

HCID 723630(3S)-5-Oxo-1-[(1S)-1-phenylethyl]pyrrolidine-3-carboxylic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 13772856HCID 13772856, compound

Procedure

(S)-5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylic acid (M3) (1.16 g, 5 mmol) was treated with CH3OH/HCl (10 mL, 1 M) for 3 h. The excess CH3OH/HCl was removed under reduced pressure. The residue was basified with saturated aqueous NaHCO3 to pH 8. The aqueous phase was extracted with ethyl acetate (50 mL×3). The combined organics were washed with brine, dried over Na2SO4 and evaporated under reduced pressure to give (S)-methyl 5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylate (M4), which was used directly in the next step. 1H NMR (300 MHz, CDCl3) δ 7.24-7.37 (m, 5H), 5.48 (q, J=7.2 Hz, 1H), 3.72 (s, 3H), 3.51-3.56 (m, 1H), 3.03-3.21 (m, 2H), 2.62-2.79 (m, 2H), 1.53 (d, J=7.2 Hz, 3H).

Workup

  1. customThe excess CH3OH/HCl was removed under reduced pressure
  2. extractionThe aqueous phase was extracted with ethyl acetate (50 mL×3)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9bf09925c4cf4c63a585a05b1e7dda69
Source dataset
uspto-grants-2012_09
Patent number
US08263605B2

Reaction notes

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