Diisopropylethylamine → Methyl (3R)-4-[2-(3,5-difluorophenyl)-2-oxoethyl]morpholine-3-carboxylate

HRID 1615842Notes

Reaction equation

HRID 1615842 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][C@@H:2]1[C:7]([O:9][CH3:10])=[O:8].[F:11][C:12]1[CH:13]=[C:14]([CH:19]=[C:20]([F:22])[CH:21]=1)[C:15](=[O:18])[CH2:16]Br.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:11][C:12]1[CH:13]=[C:14]([C:15](=[O:18])[CH2:16][N:1]2[CH2:6][CH2:5][O:4][CH2:3][C@@H:2]2[C:7]([O:9][CH3:10])=[O:8])[CH:19]=[C:20]([F:22])[CH:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514261Methyl (3R)-3-morpholinecarboxylateHCID 27783312-Bromo-1-(3,5-difluorophenyl)ethanone

Product 1

HCID 58118712Methyl (3R)-4-[2-(3,5-difluorophenyl)-2-oxoethyl]morpholine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl (3R)-morpholine-3-carboxylate from Step A (556 mg, 3.83 mmol) and 3,5-difluorophenacyl bromide (450 mg, 1.92 mmol) in CH2Cl2 (2 mL) was added DIPEA (0.669 mL, 3.83 mmol). The reaction mixture was stirred at ambient temperature for 1 h, then concentrated in vacuo. The crude product was purified on silica gel, eluting with hexane:EtOAc—75:25, to yield the title compound. MS: m/z=300 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified on silica gel
  3. washeluting with hexane

Sources & evidence

ORD record
ord-00dac3ca932d42b78e3c46f5240d8776
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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