4-Methylmorpholine → ((3As,5r,6s,6as)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone

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Reaction Steps

Step-IV: To a stirred solution of (3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid (20 g, 98 mmol) in THF (400 ml) was added TBTU (47.2 g, 147 mmol), N-methylmorpholine (NMM, 16.16 ml, 147 mmol) at room temperature and stirred for 30 min. To it was added morpholine (12.99 ml, 147 mmol) and stirred for 6 h. The solid was filtered off by filtration and it was washed with THF. The filtrate was concentrated and resulting residue was purified by silica gel column chromatography to give 17.8 g of ((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-morpholin-4-yl-methanone as a white solid. 1H NMR (400 MHz, CD3OD): δ 1.33 (s, 3H), 1.49 (s, 3H), 3.42-3.53 (m, 2H), 3.62-3.83 (m, 6H), 4.47 (d, J=2.0 Hz, 1H), 4.57 (d, J=3.6 Hz, 1H), 4.59 (d, J=2.0 Hz, 1H), 6.00 (d, J=3.2 Hz, 1H).

Provenance & Evidence