Diisopropylamine → HCID 131723198, compound

Participants

Reaction Conditions

Reaction Steps

Lithium diisopropylamide (LDA) was prepared by the addition of 2.5 M n-butyllithium in hexane (8.4 mL) to a solution of diisopropylamine (2.94 mL, 21 mmol) in THF (30 mL) at −78° C. followed by stirring at 0° C. for 20 min. A solution of methyl 4-benzyloxyphenylacetate (4.8 g, 18.7 mmol) in THF (50 mL) was cooled to −78° C. and to it was added the prepared LDA solution. The mixture was stirred at −78° C. for 1 h and t-butyl bromoacetate (3.1 mL, 21 mmol) in THF (20 mL) was added. The mixture was allowed to warm to 0° C., stirred for an additional 1.5 h at 0° C., quenched with MeOH and concentrated in vacuo. The residue was taken up in EtOAc and the solution was washed with citric acid and brine, dried over MgSO4 and concentrated. Purification on a silica gel column by eluting with 40% EtOAc/hexane afforded the desired product (6.0 g, 86%) as a solid. MS (CI—NH3): (M+H)+=371.

Provenance & Evidence