Compound 17

View in PubChem | MDL Molfile | ChemDraw

InChIKey IRRPQUWTLLNODP-QCLAVDOMSA-N

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

A solution of 10 mg (0.060 mmol, 1 eq.) azide 16, 26 mg (0.120 mmol, 2 eq.) Boc₂O and 6 mg (0.006 mmol, 0.09 eq.) 10% Pd/C in THF (5 mL) was degassed with N₂ in a sonicator for 5 minutes, then flushed with H₂ (3 ×) and stirred for 48 h at rt under H₂ atmosphere (balloon). The reaction mixture was filtered through pad of Celite and the filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography (CHCl₃:MeOH = 9:1) to yield 13.4 mg (0.056 mmol, 93%) N-Boc temuline (17) as a yellow oil (one spot on TLC). TLC (CHCl₃:MeOH:NH₄OH = 9:2:0.2), R_f = 0.66 (KMnO₄). ¹H NMR (CDCl₃, 600 MHz): δ= 5.45 (brs, 1H), 4.46 (dd, J =1.6, 4.4 Hz, 1H), 4.23 (d, J=5.6 Hz, 1H), 4.14 (s, 1H), 3.36 (d, J=11.8 Hz, 1H), 3.12–3.08 (m, 2H), 2.96–2.91 (m, 1H), 2.43 (d, J=11.8 Hz, 1H), 2.10–2.04 (m, 1H), 2.02–1.97 (m, 1H), 1.43 (s, 9H). ¹³C NMR (CDCl₃, 150 MHz): δ= 155.5, 81.0, 79.6, 74.1, 69.7, 61.0, 58.5, 54.6, 33.8, 28.3. IR (Diamond-ATR, neat) ν_max: 2974, 2937, 1697, 1547, 1365, 1289, 1251, 1161, 1152, 999, 961, 850, 794, 749, 665 cm^-1. [α]²⁵ _D + 38.7° (c= 0.35, CHCl₃). HRMS (ESI) calcd for C₁₂H₂₀N₂O₃ [M+H]⁺: 241.1547; found: 241.1545.