Water → (S)-3-((R)-1-Hydroxy-2-methylsulfanylethyl)pyrrolidine-1-carboxylic acid t-butyl ester

HRID 533388Notes

Reaction equation

HRID 533388 reaction equation
[CH3:1][S-:2].[Na+].[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([C@@H:16]2[CH2:18][O:17]2)[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].O>C1COCC1>[C:4]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C@H:13]([C@@H:16]([OH:17])[CH2:18][S:2][CH3:1])[CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 86650334(S)-(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 66859519(S)-3-((R)-1-Hydroxy-2-methylsulfanylethyl)pyrrolidine-1-carboxylic acid t-butyl esterYield 56.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium methyl mercaptide (296 mg, 4.2 mmol) was dissolved in THF (1.0 mL), and the mixture was stirred for 10 minutes at room temperature. (S)—(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (300 mg, 1.41 mmol) was dissolved in THF (0.4 mL) and added to the mixture. The resulting solution was placed in a microwave reactor for 30 minutes at 100° C., then cooled to room temperature. Hexanes (3×10 mL) was added, followed by water (10 mL). The organic layer was collected, dried over Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography (0-100% EtOAc in hexanes) to yield the title compound as a clear oil (207 mg).

Workup

  1. additionadded to the mixture
  2. waitThe resulting solution was placed in a microwave reactor for 30 minutes at 100° C.
  3. temperaturecooled to room temperature
  4. customThe organic layer was collected
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-81c689d447e94b30a9fe7c63f45e532e
Source dataset
uspto-grants-2014_10
Patent number
US08853255B2

Reaction notes

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