Diisopropylethylamine → HCID 69900480, compound

Participants

Reaction Steps

In 10 mL of DMF was added 3.0 g (16.7 mmol) of 7-Chloro-thieno[3,2-b]pyridine-2-carboxylic acid lithium salt, 3.20 g (14.66 mmol) of (2S,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride, PyBop (9.12 g (17.5 mmol) and 5.59 mL (32.1 mmol) of DIEA and the mixture was stirred for 24 h. To the mixture was added 50 mL of EtOAc was washed with 50/50 aq. NaHCO3 (2×50 mL). The organic layer was dried over Na2SO4 and concentrated to give an amber oil. Purification through 100 mL of silica eluting with EtOAc:CH2Cl2 (1:1) gave crude product. Diethyl ethyl was used to triturate (2×5 mL) the residue to afford 3.43 g (70%) of (2S,4R)-1-(7-Chloro-thieno[3,2-b]pyridine-2-carbonyl)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester as off-white solid. HPLC: Rt 3.36 min. (98.2% area). LCMS (ESI) (M+H+) m/z: 341.0.

Provenance & Evidence