HCID 25129449, compound → HCID 25129794, compound
Reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:10][CH2:11][O:12][CH2:13][CH:14]=[CH:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].O1CCCC[C@@H](O)C1>>[Si:1]([O:8][C@H:9]1[CH2:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
3
Procedure
Hydrogenolysis of 15 was carried out as described for 8e to afford (S)-4-(tert-butyldimethylsilyloxy)oxepane in 95% yield as a colourless oil: 1H NMR (CDCl3) δ 4.03-3.96 (m, 1H), 3.79-3.57 (m, 4H), 1.98-1.69 (m, 5H), 1.64-1.51 (m, 1H), 0.88 (s, 9H), 0.044 (s, 3H), 0.038 (s, 3H); 13C NMR (CDCl3) δ 70.2, 69.4, 64.2, 40.1, 34.5, 25.7, 23.7, 18.0, −4.9. Deprotection of the above compound was performed as described for compound 11 and afforded the title compound in 75% yield as a colorless oil: 1H NMR (CDCl3) δ 4.03-3.98 (m, 1H), 3.82-3.59 (m, 4H), 2.02-1.98 (m, 1H), 1.89-1.80 (m, 4H), 1.66-1.64 (m, 1H); 13C NMR (CDCl3) δ 70.5, 69.6, 64.7, 38.9, 34.9, 24.3.
Sources & evidence
- ORD record
- ord-cfff925ed1884362a1dcda9fb89f16ad
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501961B2
Reaction notes
Loading…