Reaction #531870

ord-38e807176e974e48a5fdfd80a9cb37cd

Reaction equation

[H-].[Na+]
sodium hydride
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@H](OCc2ccccc2)CC1
compound 1032
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@H](OCc2ccccc2)CC1
trans-1-(4-Benzyloxy-cyclohexyl)-3-tricyclo[3.3.1.13,7]decan-1-yl-urea
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@@H](O)CC1
compound 1077
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@@H](O)CC1
cis-1-(4-Hydroxy-cyclohexyl)-3-tricyclo[3.3.1.13,7]decan-1-yl-urea
BrCc1ccccc1
benzyl bromide
→
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@@H](OCc2ccccc2)CC1
Compound 1078
Yield 60.0%
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@@H](OCc2ccccc2)CC1
cis-1-(4-Benzyloxy-cyclohexyl)-3-tricyclo[3.3.1.13,7]decan-1-yl-urea
Yield 60.0%

Reactants

[H-].[Na+]
sodium hydride
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@H](OCc2ccccc2)CC1
compound 1032
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@H](OCc2ccccc2)CC1
trans-1-(4-Benzyloxy-cyclohexyl)-3-tricyclo[3.3.1.13,7]decan-1-yl-urea
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@@H](O)CC1
compound 1077
O=C(NC12CC3CC(CC(C3)C1)C2)N[C@H]1CC[C@@H](O)CC1
cis-1-(4-Hydroxy-cyclohexyl)-3-tricyclo[3.3.1.13,7]decan-1-yl-urea
BrCc1ccccc1
benzyl bromide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Compound 1078 (2.22 g, 60%) was synthesized from compound 1077 (0.29 g, 1 mmol) by the same method) as that described for compound 1032 with benzyl bromide (0.20 g, 1.2 mmol) and 60% sodium hydride (0.06 g, 1.5 mmol). Yield: 0.35 g (92% of theory). M.P.: 181° C. 1H NMR (300 MHz, CDCl3): δ 7.43-7.24 (m, 5H), 4.49 (s, 2H), 4.11 (d, J=8.3 Hz, 1H), 4.02 (s, 1H), 3.66-3.51 (m, 2H), 2.23-1.07 (m, 23H).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08476043B2uspto-grants-2013_07