Sodium borohydride → tert-Butyl ((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamate

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Reaction Steps

To a solution of (2S,4R)-1-tert-butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate (30 g, 0.1 mol) in MeOH/H2O (700/70 mL) was added NaBH4 (25 g, 0.66 mol), the resulting mixture was stirred 1 h at rt and quenched with sat. aq. NH4Cl (300 mL). The organic solvent was removed under vacuum and extracted with EA (3×250 mL). The combined organic phases were washed with brine (250 mL), dried over anhydrous Na2SO4, filtered and evaporated to afford the crude tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate (22 g, 85%). It was used for the next step without further purification. 1H NMR (CD3OD) δ 5.8-5.7 (m, 1H), 5.1-5.0 (m, 2H), 4.9-4.8 (d, 1H), 3.7-3.5 (m, 4H), 2.2-2.0 (m, 2H), 1.7-1.5 (m, 2H), 1.5-1.4 (s, 9H).

Provenance & Evidence