Cyclo(prolylglycyl) → (6S)-1,4-Diazabicyclo(4.3.0)nonane

HRID 2377861Notes

Reaction equation

HRID 2377861 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:13](=O)[C@@H:12]2[CH2:15][CH2:16][CH2:17][N:11]2[C:9](=O)[CH2:8]1.OC1C2C(=CN=CC=2)NC(=O)C=1C1NC2C=C(C)C=CC=2N=1>>[N:11]12[CH2:17][CH2:16][CH2:15][C@H:12]1[CH2:13][NH:7][CH2:8][CH2:9]2

Participants

4

Reactant 3

HCID 126154Cyclo(prolylglycyl)HCID 21226445Aluminium lithium hydrideHCID 1355181534-Hydroxy-3-(6-methyl-1H-benzoimidazol-2-yl)-1H-[1,7]naphthyridin-2-one

Product 1

HCID 781249(6S)-1,4-Diazabicyclo(4.3.0)nonane

Procedure

(6S)-1,4-diazabicyclo[4.3.0]nonane was synthesized as shown above by LAH (lithium aluminum hydride) reduction of commercially available Cyclo-Gly-Pro, employing the literature procedure set forth in the following reference which is herein incorporated by reference in its entirety for all purposes as if fully set forth herein: de Costa B. R. et al. J. Med. Chem., 1993, 36, 2311. Conversion to the concomitant 3-[6-((1S)-3,6-diazabicyclo[4.3.0]non-3-yl)benzimidazol-2-yl]-4-amino-5-fluorohydroquinolin-2-one was performed according to the procedure in Example 8 (LC/MS m/z 419.1 (MH+), Rt 1.96 minutes).

Sources & evidence

ORD record
ord-1d152a24766f4ae0a217dcc5c1d20f86
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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