Ethyl Acetate → HCID 86674692, compound

HRID 710276Notes

Reaction equation

HRID 710276 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O.C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[Br:21]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 67240315HCID 67240315, compound

Product 1

HCID 86674692HCID 86674692, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 100 mL round-bottomed flask, (R)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (4.3 g, 15.4 mmol) was dissolved in dimethylformamide (30 ml). N-Bromosuccinimide (2.75 g, 15.4 mmol) was added and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into ethyl acetate and extracted with saturated sodium chloride solution. The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100 g, gradient 0-50% ethyl acetate in heptane) to yield a white solid (5.2 g, 94%), MS (ISP): 301.3 ([{79Br}M-tBu+H]+), 303.4 ([{81Br}M-tBu+H]+).

Workup

  1. extractionextracted with saturated sodium chloride solution
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography (silica gel, 100 g, gradient 0-50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b97fe8754bfa46f593ff24da998a6149
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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