Methanesulfonyl chloride → HCID 86598913, compound

HRID 456760Notes

Reaction equation

HRID 456760 reaction equation
[OH:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18][CH3:19])=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[CH3:20][S:21]([O:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18][CH3:19])=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:3]1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86598902HCID 86598902, compound

Product 1

HCID 86598913HCID 86598913, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-tert-butyl 3-methyl (1R,3S,4S,6R)-6-hydroxy-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate (185 mg) in pyridine (2 mL), was added methanesulfonyl chloride (117 mg). The mixture was stirred at room temperature for 2 hrs. The resulting mixture was evaporated in vacuo. To the residue, water was added. The mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with hexane and ethyl acetate (1:1) to give the target compound (237 mg).

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. additionTo the residue, water was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with hexane and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-1d00357fe7ee4799acd614cd73b2f24b
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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