Acetaldehyde, 2,2-dimethoxy- → HCID 58168567, compound

HRID 909876Notes

Reaction equation

HRID 909876 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH:4]=O.[CH3:8][C:9]([CH3:14])([CH3:13])[C@H:10]([NH2:12])[CH3:11]>CO.[Pd]>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH:12][C@@H:10]([C:9]([CH3:14])([CH3:13])[CH3:8])[CH3:11]

Participants

5

Reactant 2

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 5324845(R)-3,3-Dimethyl-2-aminobutane

Product 1

HCID 58168567HCID 58168567, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

2,2-Dimethoxyacetaldehyde (7.54 mL) was added to a solution of (R)-3,3-dimethylbutan-2-amine (5.06 g) in methanol (20 mL) and the mixture stirred for 2 h. A slurry of palladium on carbon (10%, 200 mg) in methanol (5 mL) was added and the mixture hydrogenated at 5 bar for 66 h. The mixture was then filtered and concentrated in vacuo to afford (R)- N-(2,2-dimethoxyethyl)-3,3-dimethylbutan-2-amine (8.78 g) as an oil. 1H NMR (400 MHz, CDCl3) δ 4.47 (t, J=5.6 Hz, 1H), 3.38 (s, 3H), 3.37 (s, 3H), 2.86 (dd, J=12.2, 5.5 Hz, 1H), 2.58 (dd, J=12.1, 5.9 Hz, 1H), 2.23 (q, J=6.4 Hz, 1H), 0.97 (d, J=6.4 Hz, 3H), 0.89 (s, 9H)

Workup

  1. waitthe mixture hydrogenated at 5 bar for 66 h
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0db3c924e004b84ab7506ab59230f32
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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