Pyridine → tert-Butyl 3-carbamoylmorpholine-4-carboxylate

HRID 1161899Notes

Reaction equation

HRID 1161899 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:17]1C=CC=CC=1.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O1CCOCC1>[NH2:17][C:14]([CH:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 27601334-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid

Product 1

HCID 21098189tert-Butyl 3-carbamoylmorpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of the compound prepared in Step 1 (1 eq.), pyridine (0.6 eq.) and di-t-butyl dicarbonate (1.3 eq.) in dioxane (0.6 M), NH4HCO3 (1.26 eq.) was added and the mixture was stirred at room temperature for 20 hours. Mixture was concentrated, taken up in EtOAc and washed with water and brine. Organics were dried over Na2SO4 and evaporated giving the title product as an oil which crystallized at room temperature.

Workup

  1. concentrationMixture was concentrated
  2. washwashed with water and brine
  3. dry with materialOrganics were dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-2f15ca6eefaa4172a740aee2f25b055d
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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