Reaction #53880

ord-5b044c6697134f7598e070df0eb3de79

Reaction equation

CCNCCO
2-ethylamino-ethanol
CN[C@H]1CC[C@H](CCCCCOS(C)(=O)=O)CC1
trans-Methansulfonic acid 5-(4-methyl amino-cyclohexyl)-pentyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid
O=C(Cl)Oc1ccc(F)c(F)c1
3,4-difluoro-phenyl chloroformate
→
CCN(CCO)CCCCC[C@H]1CC[C@H](N(C)C(=O)Oc2ccc(F)c(F)c2)CC1
trans-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-methyl-carbamic acid 3,4-difluoro-phenyl ester

Reactants

CCNCCO
2-ethylamino-ethanol
CN[C@H]1CC[C@H](CCCCCOS(C)(=O)=O)CC1
trans-Methansulfonic acid 5-(4-methyl amino-cyclohexyl)-pentyl ester
O=C(O)C(F)(F)F
trifluoroacetic acid
O=C(Cl)Oc1ccc(F)c(F)c1
3,4-difluoro-phenyl chloroformate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

In analogy to examples 29.10 and 29.11, trans-Methansulfonic acid 5-(4-methyl amino-cyclohexyl)-pentyl ester.trifluoroacetic acid salt and 3,4-difluoro-phenyl chloroformate were reacted, followed by treatment with 2-ethylamino-ethanol to yield trans-(4-{5-[Ethyl-(2-hydroxy-ethyl)-amino]-pentyl}-cyclohexyl)-methyl-carbamic acid 3,4-difluoro-phenyl ester, MS: 427 (MH+).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858651B2uspto-grants-2005_02