Methylamine → Tert-butyl 2-(methylcarbamoyl)morpholine-4-carboxylate

HRID 889214Notes

Reaction equation

HRID 889214 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:17][N:18](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.CN>CN(C=O)C.C(O)C>[CH3:17][NH:18][C:14]([CH:10]1[O:11][CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)=[O:16]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×

Product 1

HCID 66760938Tert-butyl 2-(methylcarbamoyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a cold solution (ice bath) of N-Boc-2-morpholinecarboxylic acid (0.5 g, 2.16 mmol) in DMF (10 mL) was added HATU ((2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate) (0.98 g, 2.58 mmol), N,N diisopropylethylamine (2.2 g, 17.3 mmol), and 1 mL of 8 N solution of methylamine in ethanol. After the addition was finished the ice bath was removed, and the heterogeneous solution was stirred overnight at room temperature. The solution was dissolved in ethyl acetate (50 mL) and washed with a saturated solution of NaHCO3. Ethyl acetate layer was separated, dried (MgSO4) and concentrated under reduced pressure to give tert-butyl 2-(methylcarbamoyl)morpholine-4-carboxylate as an oil. MS (APCI) 245 (M+)

Workup

  1. additionAfter the addition
  2. customwas removed
  3. dissolutionThe solution was dissolved in ethyl acetate (50 mL)
  4. washwashed with a saturated solution of NaHCO3
  5. customEthyl acetate layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57c2ddf0d62245dfb2832681d705e999
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

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