Methyl cyclopent-1-ene-1-carboxylate → HCID 86607904, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

According to the procedure of Tet. Asymm., 13, 2002, 1555: To a solution of (R)-N-benzyl-N-α-methylbenzylamine (1.37 mL, 2 eq.) in THF (10 mL) at −78° C. was added n-butyllithium (2.4 M, 2.2 mL, 1.6 eq). The reaction was allowed to stir for 30 min at −78° C. and then methyl 1-cyclopentene-1-carboxylate (0.41 mL, 3.25 mmol, 1 eq) was added dropwise. The reaction was stirred for 3 h at −78° C. and then a solution of (1R)-(−)-(10-camphorsulfonyl)oxaziridine (1.49 g, 2 eq) in THF (12 mL) was added dropwise via cannula. The reaction was allowed to stir at room temperature overnight, and was then taken up in ethyl acetate, washed with NaHCO3 (1×), brine (2×), dried over Na2SO4, filtered and concentrated. Purification by silica chromatography eluting with a gradient of 10-15% ethyl acetate/hexanes afforded methyl (1R,2R)-2-{benzyl[(1R)-1-phenylethyl]amino}-1-hydroxycyclopentanecarboxylate as an off white solid (0.77 g, 69%). MS: 354.2 (M+H)+

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