Hexane → HCID 131734806, compound

HRID 1778155Notes

Reaction equation

HRID 1778155 reaction equation
[CH3:1][S@:2]([CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:3].[S:15](N)([C:18]1[CH:26]=[CH:25][C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=1)(=[O:17])=[O:16].CCCCCC>C(Cl)Cl>[S:15]([C:18]1[CH:26]=[CH:25][C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=1)([OH:3])(=[O:17])=[O:16].[CH3:1][S@@:2]([CH2:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[NH:22])=[O:3]

Participants

5

Reactant 3

HCID 8058HexaneHCID 227844-NitrobenzenesulfonamideHCID 118130042HCID 118130042, compound

Product 1

HCID 131734806HCID 131734806, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (R)-((3-(methylsulfinyl)propoxy)methyl)benzene (0.50 g, 2.36 mmol, 1 eq.) was dissolved in DCM (15 mL) followed by addition of NsNH2 (0.71 g, 3.53 mmol, 1.5 eq.) and PhIO (0.77 g, 03.53 mol, 1.5 eq.). The reaction mixture was stirred at room temperature for 10 min followed by addition of Rh2(OAc)4 (30 mg, 0.07 mmol, 0.03 eq.), stirred for 1.5 hours, and filtered. The filtered cake was slurried with DCM (30 mL). The combined DCM was concentrated to give an oil product that was reslurried with hexane to give a crude product (0.26 g) that was recrystallized from MeOH/DCM to furnish the title compound (0.148 g, 15%, 98% ee).

Workup

  1. stirringstirred for 1.5 hours
  2. filtrationfiltered
  3. concentrationThe combined DCM was concentrated
  4. customto give an oil product that
  5. customto give a crude product (0.26 g) that
  6. customwas recrystallized from MeOH/DCM

Sources & evidence

ORD record
ord-23e137864fd2487b8f055e5afb3071cf
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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