Triethylamine → tert-Butyl 3-cyanomorpholine-4-carboxylate

HRID 1161900Notes

Reaction equation

HRID 1161900 reaction equation
[NH2:1][C:2]([CH:4]1[CH2:9][O:8][CH2:7][CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=O.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[C:2]([CH:4]1[CH2:9][O:8][CH2:7][CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])#[N:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 21098189tert-Butyl 3-carbamoylmorpholine-4-carboxylate

Product 1

HCID 21098190tert-Butyl 3-cyanomorpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Step 2 (1 eq.) and triethylamine (2.1 eq.) in CH2Cl2 (0.1 M) was cooled to 0° C. and trifluoroacetic anhydride (1.1 eq.) added dropwise under nitrogen. Stirring was continued 3.5 hours more at room temperature and volatiles removed in vacuo. Residues taken in EtOAc were washed with water, brine and dried over Na2SO4. Evaporation gave the title compound as a brown solid.

Workup

  1. customvolatiles removed in vacuo
  2. washwere washed with water, brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation

Sources & evidence

ORD record
ord-73503a154c2c4edaa8da2ca3f50fc988
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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