Sodium Azide → HCID 86667162, compound

Participants

Reaction Conditions

Reaction Steps

The diastereomeric mixture of (1R,2R,6R)-2-(triphenylmethoxy)-7-oxabicyclo[4.1.0]heptane 1 (755 mg, 2.12 mmol) and the S,S-epoxide was dissolved with NaN3 (861 mg, 13.3 mmol) in H2O (1.7 mL) and MeOH (15 mL). The mixture was heated to 80° C., refluxed over night and then diluted with water and CH2Cl2. The organic layer was separated and the aqueous layer was rewashed (CH2Cl2). The entire organic layer was dried (MgSO4), filtered and concentrated. Purification was made by recrystallization in MeOH at −18° C. The reaction yielded 62% of 2. 1H-NMR (CDCl3) 7.50 (m, 6 H), 7.20-7.40 (m, 9 H), 3.69 (t, J=9.50 Hz, 1 H), 3.05 (ddd, J=4.80, 9.44, 12.05 Hz, 1 H), 2.91 (ddd, J=4.17, 8.81, 11.28 Hz, 1 H), 2.70 (s, 1 H), 1.80 (m, 1 H), 1.50 (m, 2 H), 1.20-1.40 (m, 2 H), 0.80 (m, 1 H).

Provenance & Evidence