Acetic Anhydride → (R)-tert-butyl 2-(acetamidomethyl)morpholine-4-carboxylate

HRID 594033Notes

Reaction equation

HRID 594033 reaction equation
[NH2:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.C(N(CC)CC)C.[C:23](OC(=O)C)(=[O:25])[CH3:24]>ClCCl>[C:23]([NH:1][CH2:2][C@H:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1515269(R)-2-Aminomethyl-4-Boc-morpholine

Product 1

HCID 90408801(R)-tert-butyl 2-(acetamidomethyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 2-(aminomethyl)morpholine-4-carboxylate (1.0 equiv.) and triethylamine (1.5 equiv.) in dichloromethane (0.1 M) was added acetic anhydride (1.1 equiv.). The resulting mixture was stirred at RT for 45 min. After concentration, the residue was partitioned between EtOAc and water. The organic phase was washed with water and then with brine. After drying over sodium sulfate the solution was concentrated in vaccuo to give crude (R)-tert-butyl 2-(acetamidomethyl)morpholine-4-carboxylate which was used in the next step without further purification. LCMS (m/z) (M+H)=159.1 (-Boc), Rt=0.53 min.

Workup

  1. concentrationAfter concentration
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organic phase was washed with water
  4. dry with materialAfter drying over sodium sulfate the solution
  5. concentrationwas concentrated in vaccuo

Sources & evidence

ORD record
ord-b0bdcc4b33c244a8b04a36229572618b
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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