Iodoethane → HCID 10692325, compound

HRID 225958Notes

Reaction equation

HRID 225958 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH:21]=[CH:22][C:23]([OH:25])=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH2:27][CH3:28].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Si:14]([O:13][C@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@H:9](/[CH:21]=[CH:22]/[C:23]([O:25][CH2:27][CH3:28])=[O:24])[CH2:10]1)([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 69036203HCID 69036203, compound

Product 1

HCID 10692325HCID 10692325, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-((2S,4R)-1-(tert-butoxycarbonyl)-4-{[tert-butyl(dimethyl)silyl]oxy}-pyrrolidin-2-yl)acrylic acid (40 g, 0.107 mol) in dry DMF (250 ml) was added iodoethane (17.3 ml, 0.23 mol), followed by K2CO3 (29 g, 0.22 mol). After stirring at RT for 4 h, K2CO3 was filtered off and solvent removed under vacuum. The residue was taken in dichloromethane, washed with brine and dried. The solvent was removed under vacuum to give tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]pyrrolidine-1-carboxylate (35 g) as pale yellow liquid. Yield: 82%

Workup

  1. filtrationK2CO3 was filtered off
  2. customsolvent removed under vacuum
  3. washwashed with brine
  4. customdried
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ac311e6c19b6438684852753b77b8a53
Source dataset
uspto-grants-2009_07
Patent number
US07557136B2

Reaction notes

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