Methyl iodide → HCID 67310066, compound

HRID 2061037Notes

Reaction equation

HRID 2061037 reaction equation
[CH3:1][C:2]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:10])[CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH3:19][I:20]>>[I-:20].[C:14]([O:13][C:12]([NH:11][C:2]([CH3:1])([CH3:10])[CH2:3][N+:4]1([CH3:19])[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 60134565HCID 60134565, compound

Product 1

HCID 67310066HCID 67310066, compoundYield 85%

Conditions

Temperature
50 °C

Procedure

tert-Butyl 2-methyl-1-morpholinopropan-2-ylcarbamate (640 mg, 2.5 mmol) was dissolved in methyl iodide (20 ml) and placed in a sealed tube. The reaction was stirred at 50° C. for 18 hours. The reaction mixture was concentrated and partitioned between water and ethyl acetate. The water layer was separated and concentrated to give 840 mg (85%) 4-(2-(tert-butoxycarbonylamino)-2-methylpropyl)-4-methylmorpholin-4-ium iodide. 1H NMR (D2O): δ (m, 4 H), 3.83 (s, 2 H), 3.72-3.54 (m, 4 H), 3.37 (s, 3 H), 1.50 (s, 6 H), 1.45 (s, 9 H); MS (ESI+) calculated for C14H29N2O3+: 273.22, Found: 273 (M+).

Workup

  1. customplaced in a sealed tube
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between water and ethyl acetate
  4. customThe water layer was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2375e7108c55492ebe6be28d4d4bb3bc
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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