Dimethyl Sulfide → HCID 86620350, compound

HRID 1867607Notes

Reaction equation

HRID 1867607 reaction equation
[O:1]=[O+][O-].[CH2:4]([N:7]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][CH2:9]1)[CH:5]=C.CSC>ClCCl.CO>[C:27]([O:26][C:24]([N:7]([CH2:4][CH:5]=[O:1])[CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:10][CH2:9]1)=[O:25])([CH3:29])([CH3:30])[CH3:28]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 68566766HCID 68566766, compound

Product 1

HCID 86620350HCID 86620350, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ozone (g) was bubbled into a solution of benzyl 4-[allyl(tert-butoxycarbonyl)amino]piperidine-1-carboxylate (2.75 g, 7.34 mmol) in dichloromethane (30 mL) and methanol (15 mL) at −78° C. for 17 min. Nitrogen (g) was then bubbled into the mixture for 30 min followed by the addition of dimethylsulfide (2.70 mL, 36.72 mmol). The reaction warmed to ambient temperature and stirred for 3 h. The mixture was concentrated and redissolved in ethyl acetate. The ethyl acetate layer was washed with water (2×), brine (2×), dried over sodium sulfate, filtered, and concentrated to give the title compound (2.5 g). MS 277.09 (M+1-boc group)

Workup

  1. customNitrogen (g) was then bubbled into the mixture for 30 min
  2. concentrationThe mixture was concentrated
  3. dissolutionredissolved in ethyl acetate
  4. washThe ethyl acetate layer was washed with water (2×), brine (2×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3241e77c655d4e029f70aeb48e4f62c2
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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