Water → HCID 86750456, compound

HRID 975632Notes

Reaction equation

HRID 975632 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([OH:16])[CH2:13][C@H:12]1/[CH:17]=[CH:18]\[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].O>C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:13][C@H:12]1/[CH:17]=[CH:18]\[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 67705486HCID 67705486, compound

Product 1

HCID 86750456HCID 86750456, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-4-hydroxy-2-[(Z)-2-(pyridin-3-yl)vinyl]pyrrolidine (5.2 g) in a mixture of ethyl acetate (50 ml) and triethylamine (2.90 ml) was added dropwise methanesulfonyl chloride (1.24 ml) under ice-cooling with stirring and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture were added ethyl acetate (50 ml) and water (30 ml). The organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 g) eluting with a mixture of n-hexane and ethyl acetate (1:2, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxy-2-[(Z)-2-(pyridin-3-yl)vinyl]pyrrolidine (4.14 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe resulting residue was chromatographed on silica gel (150 g)
  7. washeluting with a mixture of n-hexane and ethyl acetate (1:2, V/V)
  8. additionThe fractions containing the desired compound
  9. customwere collected
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-c1bbf297bfdd4a3f81b3c02d6ba24192
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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