Diisopropylethylamine → HCID 178428944, compound

Participants

Reaction Steps

Combine a solution of (R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dimethyl-benzyl)-4-oxo-butyraldehyde (3.0 g, 6.2 mmol) and racemic 4,5,6,7-Tetrahydro-2H-indazol-5-ylamine (0.85 g, 6.2 mmol) in Dichloroethane (50 mL) and Acetonitrile (50 mL). Treat the solution with sodium triacetoxyborohydride (6.6 g, 31 mmol) and stir 1 hr at room temperature. Treat the reaction with N,N-Diisopropylethylamine (5.6 mL, 31 mmol) and stir overnight at room temperature. Concentrate the reaction to a residue. Quench the residue with saturated sodium carbonate and extract with EtOAc. Wash the organic with brine, dry over MgSO4, filter, and remove the solvent. Purify the crude by silica gel column chromatography using CH2Cl2 and 2M Ammonia in MeOH to elute the pure product. Remove the solvent to afford 1.66 g (62%) of desired product. MS (m/e): 430 (M+1).

Provenance & Evidence