(S)-3-(dimethylamino)-2-methyl-1-(3-nitro-phenyl)-propan-1-one → (S)-3-(dimethylamino)-2-methyl-1-(3-aminophenyl)-propan-1-one

HRID 1026782Notes

Reaction equation

[CH3:1][N:2]([CH3:17])[CH2:3][C@H:4]([CH3:16])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)=[O:6].[H][H]>[Pd].CC1CCCO1>[CH3:17][N:2]([CH3:1])[CH2:3][C@H:4]([CH3:16])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1)=[O:6]

Participants

Conditions

Temperature: 2 °C

Procedure

(S)-3-(dimethylamino)-2-methyl-1-(3-nitro-phenyl)-propan-1-one (100 g, 0.423 mol), methyl-tetrahydrofuran (400 ml) and Pd/C 5%, anhydrous (4.0 g) are added into a 1 liter autoclave, at room temperature. The suspension is cooled to 0-4° C., then it is hydrogenated at 2 bars of hydrogen gas without exceeding 8° C. The conversion is monitored using HPLC and it is deemed complete when the HPLC area % of the initial product and the reaction intermediates is <0.3. Then catalyst is filtered and the solution can be used as it is in the subsequent step or concentrated under vacuum at 45-50° C. to oily residue. About 86 g of yellow to dark red oil are obtained (about 98% yield, ee≧97%, purity ≧92%).

Workup

customwithout exceeding 8° C
filtrationThen catalyst is filtered
concentrationconcentrated under vacuum at 45-50° C. to oily residue
customAbout 86 g of yellow to dark red oil are obtained (about 98% yield, ee≧97%, purity ≧92%)

Sources & evidence

ORD record: ord-d7d84980df514c30a53700661604aadf
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729308B2

Reaction notes

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