Dichloromethane → HCID 178465716, compound

HRID 713962Notes

Reaction equation

HRID 713962 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([C:22](=O)[CH3:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]([S@@:29]([NH2:31])=[O:30])([CH3:28])[CH3:27].C(Cl)Cl>[Cl-].[Na+].O>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17](/[C:22](=[N:31]\[S@@:29]([C:26]([CH3:28])([CH3:27])[CH3:25])=[O:30])/[CH3:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 66926615HCID 66926615, compound

Product 1

HCID 178465716HCID 178465716, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1-[6-(4-tert-Butyl-cyclohexyloxy)-quinolin-2-yl]-ethanone (0.2227 g, 0.0006843 mol) and (s)-(−)-2-Methyl-2-propanesulfinamide (0.0829 g, 0.000684 mol) in Methylene chloride (1.4 mL, 0.021 mol) was added Ti(OEt)4 (0.488 mL, 0.00171 mol). The reaction was stirred at room temperature for 1 d. The mixture was then cooled to 0° C., added equal volume brine, filtrate through celite, and extracted with EtOAc. After died over Na2SO4, the residue was chromatographed 0-50% EA/HE gave product (132 mg, 45%). LCMS 2.39 min m/z 429.30 ([M+1], 100%).

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. extractionextracted with EtOAc
  3. customthe residue was chromatographed 0-50% EA/HE

Sources & evidence

ORD record
ord-37f78496ca7f486980dae4695d1150ea
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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