Trifluoroacetic acid → HCID 86708543, compound

HRID 921675Notes

Reaction equation

HRID 921675 reaction equation
[I:1][CH2:2][C:3]1([CH3:20])[O:8][CH2:7][C@@H:6]2[CH2:9][N:10](C(OC(C)(C)C)=O)[CH2:11][CH2:12][N:5]2[CH2:4]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:1][CH2:2][C:3]1([CH3:20])[O:8][CH2:7][C@@H:6]2[CH2:9][NH:10][CH2:11][CH2:12][N:5]2[CH2:4]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708541HCID 86708541, compound

Product 1

HCID 86708543HCID 86708543, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(9aS)-tert-butyl 3-(iodomethyl)-3-methylhexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (108 mg, 0.273 mmol) was taken up in DCM (3 mL) and TFA (0.42 mL, 5.45 mmol) was added. The reaction was stirred at room temperature for 1 h. The solvent was removed in vacuo and the material was taken up in MeOH. The solution was loaded onto an SCX column (5 g, benzenesulfonic acid sorbent) and rinsed with MeOH, then 7N NH3/MeOH solution to release the product. The solvent was removed in vacuo give (9aS)-3-(iodomethyl)-3-methyloctahydropyrazino[2,1-c][1,4]oxazine (79 mg) as an orange oil.

Workup

  1. customThe solvent was removed in vacuo
  2. washrinsed with MeOH
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-6aa5686154bb4212a34ff5583b6a20e1
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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