Trimethylsilyl cyanide → HCID 19961153, compound
Reaction equation
[CH:1]1([CH:7]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:19][CH3:20])[C:14]=3[O:17][CH3:18])[C:9](=[O:21])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si]([C:26]#[N:27])(C)C.[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[NH2:27][CH2:26][C:9]1([OH:21])[C:10]2[C:15](=[C:14]([O:17][CH3:18])[C:13]([O:19][CH3:20])=[CH:12][CH:11]=2)[CH2:16][CH:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:8]1Participants
Procedure
2-(2',3'-Dimethoxyphenyl)-1,3-dithiane, from Step 1 of Example 1, Method B, and ethyl 3-cyclohexylpropenoate, from Step 1 of this Example, were condensed as described in Step 2 of Example 1, Method B. The adduct was treated with Raney nickel and sodium hydroxide to give the corresponding acid. The acid was cyclized with polyphosphoric acid as described in Step 6 of Example 1, Method A, to give 3-cyclohexyl-5,6-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-one. This ketone was treated with trimethylsilylcyanide in the presence of aluminum chloride and reduced with lithium aluminum hydride as described in Step 1 of Example 2 to give 1-aminomethyl-5,6-dimethoxy-1-hydroxy-3-cyclohexyl-1,2,3,4-tetrahydronaphthalene. The hydroxy group was eliminated by treatment with anhydrous hydrogen chloride in isopropyl alcohol as described in Step 2 of Example 2 to give 1-aminomethyl-3-cyclohexyl-5,6-dimethoxy-3,4-dihydronaphthalene hydrochloride, m.p. 178°-179° C.; 1H NMR (d6 -DMSO) δ: 1.0-1.4 (m, 7H), 1.5-1.9 (m, 6H), 2.0-2.2 (m, 1H), 2.5 (dd, 1H), 2.7 (dd, 1H), 3.6 (s, 3H), 3.81 (s, 3H), 5.8 (d, 1H), 6.6 (m, 2H).
Sources & evidence
- ORD record
- ord-538c6e24a7a84c2ba2753b0d5f61877b
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05621133
Reaction notes
Loading…