Water → (6-Morpholin-4-ylmethyl-pyridin-3-yl)-carbamic acid tert-butyl ester

HRID 85163Notes

Reaction equation

HRID 85163 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:9][N:8]=1)(=O)=O.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[O:24]1[CH2:25][CH2:26][N:21]([CH2:6][C:7]2[N:8]=[CH:9][C:10]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:11][CH:12]=2)[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 86653797HCID 86653797, compound

Product 1

HCID 67170692(6-Morpholin-4-ylmethyl-pyridin-3-yl)-carbamic acid tert-butyl esterYield 72.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing (5-(tert-butoxycarbonylamino)pyridin-2-yl)methyl methanesulfonate (114; 1.70 g), morpholine (48; 1.0 g, 11.3 mmol) and K2CO3 (2.30 g, 16.9 mmol) in acetonitrile (30 mL) was stirred at room temperature for 12 h. Water (30 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:ethyl acetate=1:1 to 1:3) to afford tert-butyl 6-(morpholinomethyl)pyridin-3-ylcarbamate 115 (1.20 g, 71% for two steps).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography (petroleum ether:ethyl acetate=1:1 to 1:3)

Sources & evidence

ORD record
ord-eb95b38ada9e462484096b119a6879bb
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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