Ammonia → HCID 54218223, compound

HRID 1608809Notes

Reaction equation

HRID 1608809 reaction equation
[C:1]([CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:14])[CH2:5]1)#[N:2].N.[H][H]>CO.[Ni]>[NH2:2][CH2:1][CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:14])[CH2:5]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 22851142HCID 22851142, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54218223HCID 54218223, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (4R-cis)-6-(cyanomethyl)-N,N -diethyl-2,2 -dimethyl-1,3 -dioxane-4-acetamide (10.0 g, 0.037 mol) in methanol (220 mL) containing anhydrous ammonia (3.25 g) is reacted with hydrogen gas in a Parr shaker at 30° C. in a presence of a slurry of Raney nickel A-7000 (4.2 g) . After 3 hours, uptake of hydrogen has ceased, the mixture is cooled to 0° C., the atmosphere is vented and exchanged for nitrogen, the slurry is filtered through celite, and concentrated at reduced pressure to give 9.2 g of (4R-cis)-6-(2-aminoethyl)-N,N-diethyl-2,2 -dimethyl-1,3-dioxane-4-acetamide as an oil.

Workup

  1. filtrationthe slurry is filtered through celite
  2. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-d277dd25f37c4e16b5adb4562b71a6e9
Source dataset
uspto-grants-1995_03
Patent number
US05397792

Reaction notes

Loading…