Hexane → HCID 131734807, compound

HRID 1778157Notes

Reaction equation

HRID 1778157 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 118130114HCID 118130114, compound

Product 1

HCID 131734807HCID 131734807, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-((3-(methylsulfinyl)propoxy)methyl)benzene (0.5 g, 2.36 mmol, 1 eq.) was dissolved in DCM (1.5 L) 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 the crude title compound (0.26 g) that was recrystallized from MeOH/DCM to furnish the title compound (0.141 g, 15%, 97.78% 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 the crude title compound (0.26 g) that
  6. customwas recrystallized from MeOH/DCM

Sources & evidence

ORD record
ord-51cf0e6b445b4f19b465e05e247a5649
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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