Sodium methanethiolate → (R)-3-((S)-1-Hydroxy-2-methylsulfanylethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

HRID 1026178Notes

Reaction equation

HRID 1026178 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C@H:13]2[CH2:15][O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S-:17].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C@H:13]([OH:14])[CH2:15][S:17][CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 86664073(R)-(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 66975342(R)-3-((S)-1-Hydroxy-2-methylsulfanylethyl)pyrrolidine-1-carboxylic Acid t-Butyl EsterYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

(R)—(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (1.0 g, 4.7 mmol, 1.0 eq.) in DMF (10 mL) was combined with sodium methyl mercaptide (2.5 g, 14.1 mmol, 3.0 eq.), and the resulting mixture was stirred at 50° C. for 3 hours under nitrogen. Upon completion of the reaction, the mixture was concentrated under vacuum, extracted with EtOAc, washed with saturated aqueous NaCl and water, dried, and concentrated. The crude product was purified by preparative HPLC (MeCN:EtOH=4:6) to yield the title compound (700 mg).

Workup

  1. customUpon completion of the reaction
  2. concentrationthe mixture was concentrated under vacuum
  3. extractionextracted with EtOAc
  4. washwashed with saturated aqueous NaCl and water
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative HPLC (MeCN:EtOH=4:6)

Sources & evidence

ORD record
ord-20b679478bd7465790d55aaf28246c49
Source dataset
uspto-grants-2014_05
Patent number
US08729119B2

Reaction notes

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