Ammonia → HCID 67087187, compound

HRID 2365530Notes

Reaction equation

HRID 2365530 reaction equation
[NH2:1][CH:2]([CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@@H:16]2[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]2)=[CH:10][CH:9]=1)[C:3]#[N:4].N.[H][H]>CO.[Ni]>[CH3:21][C:18]1([CH3:22])[O:17][C@H:16]([CH2:15][O:14][C:11]2[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][CH2:5][CH:2]([NH2:1])[CH2:3][NH2:4])=[CH:9][CH:10]=2)[CH2:20][O:19]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 66917020HCID 66917020, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67087187HCID 67087187, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-amino-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-pentanenitrile (1.7 g, 4.28 mmol) in a 2M ammonia in methanol solution (50 ml) is passed through a H-CUBE apparatus fitted with a Raney nickel CatCart at 50° C. and a hydrogen pressure of 50 bar and a flow rate of 1.5 ml/min. After 5 hours of continuous cycling of the solution the reaction mixture is concentrated in vacuo to give 5-[4-((R)-2,2-Dimethyl-[1,3]dioxolane-4-ylmethoxy)-phenyl]-pentane-1,2-diamine as a light-yellow oil; [M+H]+ 309

Workup

  1. concentrationAfter 5 hours of continuous cycling of the solution the reaction mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-fd5628bac9f545c486bbf7facbaae221
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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