Sodium Bicarbonate → 4-(methoxycarbonyl)phenyl (3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine-1-carboxylate

HRID 732650Notes

Reaction equation

HRID 732650 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[CH2:13][NH:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].Cl[C:26]([O:28][C:29]1[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=1)=[O:27]>O1CCCC1.O>[Si:1]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[CH2:13][N:12]([C:26]([O:28][C:29]2[CH:30]=[CH:31][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:37][CH:38]=2)=[O:27])[CH2:11]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 854163Methyl 4-[(chlorocarbonyl)oxy]benzoate2×HCID 68913849(3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine

Product 1

HCID 866285334-(methoxycarbonyl)phenyl (3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A 350 mg portion of (3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine and 470 mg of sodium bicarbonate were suspended in 20 ml of a tetrahydrofuran-water (3:1) mixed solvent, and 320 mg of methyl 4-[(chlorocarbonyl)oxy]benzoate (mfd. by Fluka) was added in one portion thereto at room temperature. After 1Hour of stirring at room temperature, 80 mg of methyl 4-[(chlorocarbonyl)oxy]benzoate was further added thereto at room temperature. After 2 hours of further stirring, the reaction solution was concentrated under a reduced pressure. The residue was separated by diluting it with water and diethyl ether, and then extracted with diethyl ether. The organic layer was washed with water and saturated brine in that order and dried with anhydrous sodium sulfate. This was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-ethyl acetate) to obtain 571 mg of 4-(methoxycarbonyl)phenyl (3R,4R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-furyl)pyrrolidine-1-carboxylate as a colorless oily substance.

Workup

  1. additionwas added in one portion
  2. customat room temperature
  3. customat room temperature
  4. concentrationthe reaction solution was concentrated under a reduced pressure
  5. customThe residue was separated
  6. additionby diluting it with water and diethyl ether
  7. extractionextracted with diethyl ether
  8. washThe organic layer was washed with water and saturated brine in that order
  9. dry with materialdried with anhydrous sodium sulfate
  10. concentrationThis was concentrated under a reduced pressure
  11. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-ethyl acetate)

Sources & evidence

ORD record
ord-c0472953b06e422fa038fcb1cf509e4a
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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