Ethyl Acetate → HCID 53824424, compound

HRID 975668Notes

Reaction equation

HRID 975668 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O-:16])=[O:15])[C@H:11]([CH2:17][C:18]2[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC(O[CH2:28][CH:29]=[CH2:30])=O.[OH-].[Na+].C(OCC)(=O)C>O1CCCC1.O>[CH2:30]([O:15][C:14]([N:12]1[CH2:13][C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH2:10][C@H:11]1[CH2:17][C:18]1[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=1)=[O:16])[CH:29]=[CH2:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 22870379HCID 22870379, compound

Product 1

HCID 53824424HCID 53824424, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2R,4R)-4-(t-butyldimethylsilyloxy)-2-{(1-methylimidazol-2-yl)methyl}pyrrolidineformate (20.0 g) in tetrahydrofuran (300 ml) and water (200 ml) was added dropwise a solution of allyl chloroformate (7.45 ml) in THF (20 ml), adjusting pH to 9.0~9.5 with 5N-aqueous sodium hydroxide solution, at -3°~1° C. over 10 minutes. The mixture was stirred at the same temperature for 50 minutes. To the reaction mixture was added ethyl acetate (600 ml) and ice water (400 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 ml). The combined organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give (2R,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-{(1-methylimidazol-2-yl) methyl}pyrrolidine (20.5 g) as an oil.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (100 ml)
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b19a0dbbf8844780a0c9f19003154258
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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