Triethylamine → HCID 86708544, compound

HRID 921676Notes

Reaction equation

HRID 921676 reaction equation
I[CH2:2][C:3]1([CH3:13])[O:8][CH2:7][C@@H:6]2[CH2:9][NH:10][CH2:11][CH2:12][N:5]2[CH2:4]1.CCN(CC)CC>CO.[Pd]>[CH3:2][C:3]1([CH3:13])[O:8][CH2:7][C@@H:6]2[CH2:9][NH:10][CH2:11][CH2:12][N:5]2[CH2:4]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86708543HCID 86708543, compound

Product 1

HCID 86708544HCID 86708544, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(9aS)-3-(iodomethyl)-3-methyloctahydropyrazino[2,1-c][1,4]oxazine (53 mg, 0.179 mmol) was dissolved in MeOH (5 ml) and Et3N (0.037 mL, 0.268 mmol) was added. The flask was purged with Ar, and Pd/C (19.05 mg, 0.018 mmol) was added. A balloon with H2 was attached and the flask was evacuated and filled with H2 3×. The reaction was stirred over the weekend. The reaction mixture was filtered through celite, rinsing with MeOH. The solvent was removed in vacuo to give (S)-3,3-dimethyloctahydropyrazino[2,1-c][1,4]oxazine (20 mg) as a yellow solid. The crude material was taken onto the next step.

Workup

  1. additionwas added
  2. customthe flask was evacuated
  3. additionfilled with H2 3×
  4. filtrationThe reaction mixture was filtered through celite
  5. washrinsing with MeOH
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f1d7065f116444a7a5c9b7c946a9c964
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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