Lawesson's reagent → (2S)-2-t-butyldimethylsilyloxymethyl-1-methyl-5-thioxopyrrolidine

HRID 1650296Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][C:12](=O)[N:11]1[CH3:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>O1CCCC1>[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:14][CH2:13][C:12](=[S:26])[N:11]1[CH3:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (2S)-2-t-butyldimethylsilyloxymethyl 1-methyl-5-pyrrolidone (16 g) in tetrahydrofuran (160 ml) was added Lawesson's Reagent [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] (14.6 g) at ambient temperature. After stirring at 60° C. under nitrogen for 1 hour, the solvent was removed. The residue was chromatographed on silica gel eluting with a mixture of acetone and dichloromethane (1:9 V/V) to give (2S)-2-t-butyldimethylsilyloxymethyl-1-methyl-5-thioxopyrrolidine (17.0 g).

Workup

customthe solvent was removed
customThe residue was chromatographed on silica gel eluting with a mixture of acetone and dichloromethane (1:9 V/V)

Sources & evidence

ORD record: ord-24164014a8914facb78dd83063566fb0
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923857

Reaction notes

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