Reaction #12054

ord-57da838f35c74f14a87b06442b53cb79

Reaction equation

CCC(O)c1ccc2c(n1)N1C(C)CN(C(=O)OC(C)(C)C)CC1C2
6-(1-hydroxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester
BrCC1CC1
cyclopropylmethyl bromide
→
CCC(OCC1CC1)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2
product
CCC(OCC1CC1)c1ccc2c(n1)N1[C@@H](CNC[C@H]1C)C2
(4R,9aR)-6-(1-(RS)-Cyclopropylmethoxy-propyl)-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene

Reactants

—
(4R,9aR)-6-(1-(RS)-Cyclopropylmethoxy-propyl)-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene di-trifluoroacetate
CCC(O)c1ccc2c(n1)N1C(C)CN(C(=O)OC(C)(C)C)CC1C2
6-(1-hydroxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester
BrCC1CC1
cyclopropylmethyl bromide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

(4R,9aR)-6-(1-(RS)-Cyclopropylmethoxy-propyl)-4-methyl-1,2,3,4,9,9a-hexahydro-2,4a,5-triaza-fluorene di-trifluoroacetate (32 mg) was made from 6-(1-hydroxy-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (52 mg), using cyclopropylmethyl bromide (29 μl) in place of methyl iodide, according to the procedures described in Example 63 to afford the product as a colorless oil. HPLC [Xterra; 50/80; 255 nm] 100%, 1.44 min; MS (ES) 302.1 (MH+).

Source

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