Ethyl Acetate → (S)-tert-butyl 2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate

HRID 710271Notes

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.[Cl: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[Cl:21]

Participants

Conditions

Temperature: 60 °C

Procedure

In a 150 mL round-bottomed flask, (S)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (5 g, 18 mmol) was dissolved in dimethylformamide (30 ml). N-Chlorosuccinimide (2.4 g, 18 mmol) was added and the mixture was stirred at 60° C. 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, 30% ethyl acetate in heptane) to yield a light yellow solid (4.0 g, 71%) MS (ISP): 313.1 ([{35Cl}M+H]+), 315.1 ([{37Cl}M+H]+).

Workup

extractionextracted with saturated sodium chloride solution
dry with materialThe organic layers were dried over MgSO4
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography (silica gel, 100 g, 30% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-85e87563c89048779e0c3a8ff2781380
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181230B2

Reaction notes

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