N-cyclopropyl-2,2-dimethyl-propanamide → HCID 178447201, compound

Temperature

70 °C

A mixture of 3,4,7,8-tetramethyl-1,10-phenanthroline (46.9 mg, 71 µmol) and [Ir(OMe)(cod)]2 (33.5 mg, 0.14 mmol) in cyclohexane (5 mL) was stirred at room temperature for 15 min in a Schlenk flask under N2 atmosphere. N-Cyclopropylpivalamide (1a: 2.0 g, 14 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin: 3.08 mL, 21 mmol) and cyclohexane (20 mL) were added to the mixture under N2 flow. Then, the reaction mixture was heated at 80 °C for 18 h under N2 atmosphere. The reaction mixture was concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography (chloroform/acetone = 25:1 to 20:1). The collected fractions were purified again by silica gel column chromatography (hexane/ether = 1:2 to 1:4) to give 2.33 g of the product 2a as a white solid in a 62% yield. NOE was observed between H1 and H2 . This result indicates that boronate 2a has cis configuration.

ORD record

ord-8e50df18423744908ef8310fe5a135df

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201409186