Pivaloyl chloride → HCID 66734028, compound

Participants

Reaction Steps

A colourless solution of (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (660 g; J. Org. Chem. (2003), 68, 3923-3931) in DCM (6.6 l) was cooled down to 0° C. and treated with TEA (510 ml) and, dropwise, with pivaloyl chloride (378 ml). The reaction mixture was stirred for 24 h at rt. The reaction mixture was cooled to −8° C. and treated with DIPEA (1506 ml). A solution of sulfur trioxide pyridine complex (1036 g) in DMSO (4 l) was added dropwise over 90 min. The reaction mixture was stirred at 0° C. for 1 h and was quenched with the addition of water (41). The aq. layer was extracted with Et2O/Hex (1:1; 2×1 l) and the combined org. layers were concentrated in vacuo. The residue obtained after work up (Et2O/Hex 1:1) was crystallized from Hex (2 l) affording 675 g (74%) of a colourless powder.

Provenance & Evidence