(1α,2β,4β,5α)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7α-ol synthesis

Yield:-

Steps:

Multi-step reaction with 11 steps
1: NaH / tetrahydrofuran / 15 h / 50 °C
2: 63 percent / LiCl, p-benzoquinone, glacial acetic acid / Pd(OAc)2 / acetic acid / 36 h
3: 79 percent / dimethylsulfoxide / 3 h / 80 °C
4: 84 percent / 2M NaOH / methanol / 4 h / Heating
5: 94 percent / imidazole / dimethylformamide / 4 h / 0 °C
6: 96 percent / m-CPBA / CHCl₃ / 1) 0 deg C, 1h, 2) 20 deg C, 2h, 3) refrigerator, overnight
7: 95 percent / Bu₄NF / tetrahydrofuran / 20 h / Ambient temperature
8: Et₃N / tetrahydrofuran / 2 h / Ambient temperature
9: K₂CO₃ / methanol / 120 h
10: 1) naphthalene, Na / 1) DME, -78 deg C, 40 min, 2)a) -78 deg C, 15 min, b) r.t., 40 min
11: 100 percent / MeSO₃H, H₂ / 10percent Pd/C / methanol / 4 h / 760 Torr / Ambient temperature

References:

Schink, Hans E.;Pettersson, Helena;Baeckvall, Jan-E. [Journal of Organic Chemistry,1991,vol. 56,# 8,p. 2769 - 2774]

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