Morpholine → HCID 69217123, compound

HRID 2053408Notes

Reaction equation

HRID 2053408 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH2:13]([O:15][C:16](=[O:23])[CH2:17][C:18]1[NH:19][CH:20]=[CH:21][CH:22]=1)[CH3:14].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CCN(CC)CC>C1(C)C=CC=CC=1>[CH2:13]([O:15][C:16](=[O:23])[CH2:17][C:18]1[NH:19][C:20]([C:2]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:4])=[CH:21][CH:22]=1)[CH3:14]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 220944ethyl 2-(1H-pyrrol-2-yl)acetate

Product 1

HCID 69217123HCID 69217123, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Triphosgene (1.64 g, 5.5 mmol) was added to (1H-pyrrol-2-yl)-acetic acid ethylester (prepared following the general procedure described in; J. Org. Chem., 59(18),5230-5234, 1994) (841.0 mg, 5.5 mmol) in toluene (50 mL). The reslting mixture was heated at 100° C. for 1 hr. The reaction mixture was allowed to cool to RT and morpholine (1 mL) and Et3N (1 mL) was added. The resulting mixture was stirred at RT overnigbht and concentrated. The residue obtained was chromatographed on silica (50-100% EtOAc:Hexane) to obtain [5-(Morpholine-4-carbonyl)-1H-pyrrol-2-yl-acetic acid ethyl ester. Yield 43%. 1H-NMR (CDCl3; 400 MHz) δ 10.46 (brs, 1H), 6.43 and 6.08 (dd, J1=3.6, J2=2.68, 1H each), 4.1 (q, J=7.16, 2H), 3.85 and 3.73 (m, 4H each), 3.67 (s, 2H), 1.25 (t, J=7.16, 3H).

Workup

  1. customprepared
  2. temperatureto cool to RT
  3. concentrationconcentrated
  4. customThe residue obtained
  5. customwas chromatographed on silica (50-100% EtOAc:Hexane)

Sources & evidence

ORD record
ord-c577fdb0827945e0b868ebbb04e5dbc0
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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