Sodium Bicarbonate → HCID 67312716, compound

HRID 1010912Notes

Reaction equation

HRID 1010912 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@@:12]1([CH3:19])[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[OH:14][CH2:13][C@:12]1([CH3:19])[CH2:16][CH2:17][CH2:18][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 18604408HCID 18604408, compound

Product 1

HCID 67312716HCID 67312716, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution obtained by dissolving 840 mg of the compound [63-1] in 16 mL of tetrahydrofuran, 4.31 mL of a borane-methyl sulfide complex (a 2 M tetrahydrofuran solution) was added at room temperature, and the mixture was heated under reflux for 4 hours. To the reaction solution, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 to 60/40) to obtain 498 mg of benzyl (2S)-2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate [63-2] (hereinafter, referred to as the compound [63-2]).

Workup

  1. customTo a solution obtained
  2. additionwas added at room temperature
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 4 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe obtained organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe insolubles were filtered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 to 60/40)

Sources & evidence

ORD record
ord-73b011ab4834440a968cb7c9d56dfd28
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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