Water → (S)-3-((R)-2-Ethylsulfanyl-1-hydroxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

HRID 1254993Notes

Reaction equation

[CH2:1]([SH:3])[CH3:2].[H-].[Na+].[C:6]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C@H:15]([C@@H:18]2[CH2:20][O:19]2)[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].O>C1COCC1>[C:6]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C@H:15]([C@@H:18]([OH:19])[CH2:20][S:3][CH2:1][CH3:2])[CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethanethiol (312 μL, 4.2 mmol) was dissolved in THF (1.0 mL), and the mixture was cooled to 0° C. NaH (50.6 mg, 2.1 mmol) was slowly added in four portions and the mixture was stirred at room temperature for 10 minutes. (S)—(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (300 mg, 1.4 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 (315 mg).

Workup

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

Sources & evidence

ORD record: ord-e59fa386894d4b198621edf4e97c7a0f
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455665B2

Reaction notes

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