HCID 67508230, compound → HCID 86665522, compound

HRID 1770706Notes

Reaction equation

HRID 1770706 reaction equation
[Cl-:1].C(OC([NH:12][C:13]([CH3:24])([CH3:23])[CH2:14][CH2:15][N+:16]([CH2:19][CH2:20][O:21][CH3:22])([CH3:18])[CH3:17])=O)C1C=CC=CC=1>[Pd].CO>[Cl-:1].[NH2:12][C:13]([CH3:24])([CH3:23])[CH2:14][CH2:15][N+:16]([CH2:19][CH2:20][O:21][CH3:22])([CH3:17])[CH3:18]

Participants

4

Reactant 1

HCID 67508230HCID 67508230, compound

Product 1

HCID 86665522HCID 86665522, compoundYield 106.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, palladium on carbon (10%, 280 mg) was added to a solution of 3-(((benzyloxy)carbonyl)amino)-N-(2-methoxyethyl)-N,N,3-trimethylbutan-1-aminium chloride (1.3 g, 3.5 mmol) in 12 mL of methanol. The flask was degassed and placed under a hydrogen atmosphere, stirring for 18 hours at room temperature. The suspension was filtered through a pad of Celite® washing with methanol, and the filtrate was concentrated under reduced pressure to give about 835 mg of a clear oil. 1H NMR (D2O, 400 MHz) δ 1.15 (s, 6H), 1.87-1.92 (m, 2H), 3.06 (s, 6H), 3.30 (s, 3H), 3.39-3.43 (m, 2H), 3.49-3.51 (m, 2H), 3.79-3.80 (m, 2H); LRMS (ESI/APCI) m/z 189 [M]+

Workup

  1. customThe flask was degassed
  2. filtrationThe suspension was filtered through a pad of Celite®
  3. washwashing with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-805786e35e774f01a04aba0ff6b108fc
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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