Diisopropylethylamine → HCID 86658044, compound

HRID 245352Notes

Reaction equation

HRID 245352 reaction equation
[C:1]([SiH2:5][O:6][C:7](C1C=CC=CC=1)(C1C=CC=CC=1)[C:8]1[C:9]([N:18]2[CH2:23][C@H:22]([CH3:24])[O:21][C@H:20]([CH3:25])[CH2:19]2)=[C:10]([F:17])[C:11]([F:16])=[C:12]([CH:15]=1)[CH:13]=O)([CH3:4])([CH3:3])[CH3:2].CCN([CH:44]([CH3:46])[CH3:45])C(C)C.Cl.[NH2:48][OH:49]>C1COCC1.C(Cl)Cl>[Si:5]([O:6][CH2:7][C:8]1[C:9]([N:18]2[CH2:23][C@H:22]([CH3:24])[O:21][C@H:20]([CH3:25])[CH2:19]2)=[C:10]([F:17])[C:11]([F:16])=[C:12]([CH:13]=[N:48][OH:49])[CH:15]=1)([C:1]([CH3:2])([CH3:4])[CH3:3])([C:45]1[CH:44]=[CH:46][CH:3]=[CH:1][CH:2]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:15]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 178461508HCID 178461508, compound2×

Product 1

HCID 86658044HCID 86658044, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-bath cooled and stirred solution of 5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-((2R,6S)-2,6-dimethyl-morpholin-4-yl)-2,3-difluoro-benzaldehyde (Intermediate 4, 9.1 g, 17 mmol) in THF was added DIPEA (4.5 mL, 26 mmol) followed by hydroxylamine hydrochloride (1.3 g, 19 mmol) over a period of 15 min. The mixture was brought to room temperature and stirred for 12 hours. The reaction mixture was diluted with CH2Cl2 and washed successively with 1 N HCl (1×250 mL), water and brine. The organic layer dried (Na2SO4), filtered and concentrated. The residue was purified over a silica gel flash column using a gradient of ethyl acetate in pet. ether to give the title compound as white solid. Yield: 8.9 g, (86%).

Workup

  1. temperatureTo an ice-bath cooled
  2. customwas brought to room temperature
  3. washwashed successively with 1 N HCl (1×250 mL), water and brine
  4. dry with materialThe organic layer dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified over a silica gel flash column

Sources & evidence

ORD record
ord-80e46014516345e8ac2338ef18c3c8a1
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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