Ethanol → Ammonium Hydroxide

HRID 1789669Notes

Reaction equation

HRID 1789669 reaction equation
[CH2:1]1[C@H:13]2[C@H:4]([N:5]([CH2:14][C:15]#[N:16])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12]2)[CH2:3][CH2:2]1.[H][H].C([OH:21])C>[Rh]>[OH-:21].[NH4+:5].[CH2:1]1[C@@H:13]2[C@H:4]([N:5]([CH2:14][CH2:15][NH2:16])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 702EthanolHCID 21036487HCID 21036487, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 14923Ammonium HydroxideHCID 11264407HCID 11264407, compound

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

Catalytic hydrogenation of Cis(1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-acetonitrile (0.23 g, 1.08 mmol) in the presence of 5% Rh on Alumina and hydrogen (45 psi) in a 1:1 mixture of ethanol : ammonium hydroxide (40 ml) afforded the title compound. The reaction mixture was filtered through celite concentrated in vacuo and purified by flash chromatography (10% 2N NH3 in ethanol/dichloromethane) and converted to the HCl salt to give a white solid. The same step 4 procedure was used to prepare the trans isomer except that Trans (1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-acetonitrile was used instead of the cis isomer.

Sources & evidence

ORD record
ord-fde3681bcdbb4c189e247c37b32a2948
Source dataset
uspto-grants-2006_07
Patent number
US07071185B2

Reaction notes

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