Reductive Amination
Part 1: Reductive Amination Catalysts
Part 2: Asymmetric Reductive Amination Catalysts

Reductive Amination Catalysts⚫

Preparation of primary, secondary or tertiary amines fromcarbonyl compounds⚫

High catalytic activity⚫

Using formic acid as a hydrogen source⚫

High functional group tolerance (e.g., -NO2, -CN, -Br…)Iridium Complexes for Reductive Amination

Please see this brochure for details https://www.kanto.co.jp/dcms_media/other/OFC-05-EN.pdf

Typical Procedure

To a solution of ketone 1 (20 mmol) in methanol (10 mL) was added ammonium formate (3.78 g, 60 mmol), formic acid (1.51 mL,40 mmol) and Ir-PA2 (1.29 mg, 0.02 mmol) under Ar atmosphere. After stirring for 4 h under reflux, the solvent was evaporated undera vacuum. An aqueous solution of NaOH was added to the resulting residue and extracted with CH2Cl2. The combined organic
extracts were dried over Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography toafford amine 2 (90% yield).

Substrate Scope

Application

Structure

Product No.

Package

Structure

Product No.

Package07429-68

100 mg07429-95

500 mg07964-68

100 mg07964-95

500 mg07966-68

100 mg07966-95

500 mgReductive Amination Catalysts

Ir-PA1

Ir-PA3

Ir-PA5Ir-QN107127-68

100 mg07127-95

500 mg07430-68

100 mg07430-95

500 mg07965-68

100 mg07965-95

500 mg07128-68

100 mg07128-95

500 mgIr-PA2

Ir-PA4Ir-QN2Asymmetric Reductive Amination Catalysts

J. Org. Chem. 2022, 87, 8458–8468.
Org. Lett. 2024, 26, 1426–1431.

Chiral Iridium Complexes for Asymmetric Reductive Amination⚫ Preparation of chiral primary amines (b-aminotetralins, a-amino acids …)⚫ Using chiral amino alcohol as a chiral auxiliary⚫ Easy removal of chiral auxiliaries under mild oxidative conditions⚫ High catalytic activity and diastereoselectivity⚫ Using formic acid as a hydrogen source
Please see the brochure for details https://www.kanto.co.jp/dcms_media/other/OFC-12_EN.pdf

Typical procedure

To a mixture of ketone 1 (966 mg, 4.97 mmol), (R)-phenylglycinol (828 mg, 6.04 mmol) and HCO2H (566 µL, 15.0 mmol) in MeOH (5mL) was added (S)-Ir-PSA18 (0.168 mg, 0.252 µmol) under Ar atmosphere. The reaction vessel was connected to inert gas line ofballoon because of CO2 gas evolution during the reaction. After stirring for 18 h at 40 °C, the reaction was quenched by adding a sat.
NaHCO3 aq., and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, andconcentrated in vacuo. To a mixture of this crude material, 40% MeNH2 aq. (5.0 mL, 60 mmol) in MeOH/H2O (1/1, 30 mL) was added
H5IO6 (3.77 g, 16.5 mmol). After stirring for 18 h, the reaction was quenched by adding a sat. NaHCO3 aq. and 10% (w/w) Na2S2O3 aq.,
and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated
in vacuo. The residue was purified by flash column chromatography to afford optically active amine (S)-2 (889 mg, 91%, 95% ee).

Substrate Scopea N-Fmoc amide could be obtained by sequential Fmoc-amidation.

Large Scale Reaction

Direct Asymmetric Reductive Amination to N-Alkylamines

Structure

Product No.

Package

Structure

Product No.

Package

Asymmetric Reductive Amination Catalyst, Reagents
07658-68

100 mg(S)-Irr-PSA36

NaIO4

Sodium periodate

07071-68

100 mg42247-2A

5g

42247-3A

25 g

18382-1A5g

D(-)-α-Phenylglycinol

18382-2A

25 g

H5IO632061-30

25 g

100 mg(S)-Ir-PSA18(S)-(+)-Phenylglycinol

100 mg(R)-Ir-PSA36

07060-68

L-Valinol

07035-68(R)-Ir-PSA18

44078-525g

44078-32

25 g30757-1A

1g

30757-2A

5g

37233-30

25 g37233-20

100 g37233-00

500 g(R)-(-)-2-Amino-3-methyl-1-butanolOrthoperiodic acidWe provide not only reagents, but also bulk chemicals, contract synthesis, contract development andcatalyst screening services. We are ready to help your research and industrial production.

We provide not only reagents, but also bulk chemicals, contract
synthesis, contract development and catalyst screening services.
We are ready to help your research and industrial production.

Our Products (Catalysts and Ligands)
https://www.kanto.co.jp/english/products/organics/organic03.html

Product Examples We can Offer••••

We can also supply these compounds in bulk scale.
Both enantiomers are available.
Only a part of products is listed here.
If you need other compounds, please feel free to contact us.

Ligand Examples We can Offer• Both enantiomers are available.
• Only a part of ligands is listed here.
• If you need other ligands, please feel free to contact us.