Reaction #12009

ord-1a8b29b5053c40f587e0586b30fa4d8a

Reaction equation

C[C@@H]1CNC(=O)c2cc3ccc(Cl)nc3n21
intermediate b
C[C@@H]1CNC(=O)c2cc3ccc(Cl)nc3n21
(R)-6-chloro-4-methyl-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one
C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21
(R)-6-bromo-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester
[BH3-]C#N.[Na+]
sodium cyano borohydride
→
C[C@@H]1CN(C(=O)OC(C)(C)C)C[C@H]2Cc3ccc(Br)nc3N21
(4R,9aR)-6-Bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Reactants

C[C@@H]1CNC(=O)c2cc3ccc(Cl)nc3n21
intermediate b
C[C@@H]1CNC(=O)c2cc3ccc(Cl)nc3n21
(R)-6-chloro-4-methyl-3,4-dihydro-2H-2,4a,5-triaza-fluoren-1-one
C[C@@H]1CN(C(=O)OC(C)(C)C)Cc2cc3ccc(Br)nc3n21
(R)-6-bromo-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester
[BH3-]C#N.[Na+]
sodium cyano borohydride

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

This compound was prepared in analogy to Example 2, intermediate b) from (R)-6-bromo-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester and sodium cyano borohydride.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07098337B2uspto-grants-2006_08