Compound 21

Benzyl methyl carbonate

From: An efficient synthesis of loline alkaloids

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InChIKey ZGEPKHDCMGFQQP-UHFFFAOYSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

To a solution of 2.30 g (7.62 mmol, 1 eq.) azido alcohol 13 in MeOH (1.4 L) at 0 °C was added 390 μL (7.62 mmol, 1 eq.) Br2. The reaction mixture was stirred under exclusion of light (to avoid radical reactions) for 12 h at 0 °C and concentrated in vacuo. The crude product was triturated with Et2O (200 mL) and the formed precipitate was filtered off to yield 2.40 g (7.40 mmol, 97%) bromo pyrrolizidine hydrobromide 14 as colorless crystals. The filtrate was concentrated in vacuo to yield 1.20 g (7.24 mmol, 95%) carbonate 21.

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