1,2-Dichloroethane → (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Participants

Reaction Steps

Boc-D-Tic-OH (4.50 g, 16 mmol), methoxymethylamine hydrochloride (1.56 g, 16 mmol), HOBT (2.43 g, 18 mmol), EDC (3.45 g, 18 mmol), DMAP (200 mg, 1.6 mmol), DIPEA (4.2 ml) and THF (150 ml) are combined, and the resulting mixture is stirred for about 18 hours at r.t. The mixture is stripped to dryness, and the resulting residue is taken up in ethyl acetate and then washed with aqueous HCl (1N), aqueous sodium bicarbonate and brine, which is then dried over sodium sulfate. The solvent is removed and the residue is chromatographed on normal phase (ethylacetate/hexanes 1:1) to give about 3.89 g of Boc-D-Tic-NMeOMe (Weinreb amide).

Provenance & Evidence