(2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate → HCID 10979991, compound

HRID 406495Notes

Reaction equation

HRID 406495 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[CH2:21]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH-](CC)CC)C.[Li+]>C1COCC1>[Si:14]([O:13][C@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([CH3:21])[CH2:10]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 14117008(2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylateHCID 23664628Lithiumtriethylborohydride

Product 1

HCID 10979991HCID 10979991, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S,4R)-tert-butyl-4-(tert-butyldimethylsilyloxy)-2-((methylsulfonyloxy)methyl)pyrrolidine-1-carboxylate (5.34 g, 13.0 mmol) in THF (30 mL) was cooled to about 0° C. and a solution of lithium triethylborohydride (1M in THF, 52 mL) was added dropwise. The ice-bath was removed and the reaction mixture was stirred at ambient temperature for about 2 hours. The reaction mixture was cooled to about 0° C. and additional lithium triethylborohydride solution (10 mL) was added. The reaction mixture was stirred at ambient temperature for about 1 h and then the reaction was quenched by a dropwise addition of water. EtOAc (100 mL) was added and the layers were separated. The organic phase was washed with water (75 mL), IN phosphoric acid (2×100 mL), water (100 mL), aqueous sodium bicarbonate (100 mL) and brine (100 mL) then dried over magnesium sulfate and concentrated to give (2R,4R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-methylpyrrolidine-1-carboxylate that was used without further purification.

Workup

  1. customThe ice-bath was removed
  2. temperatureThe reaction mixture was cooled to about 0° C.
  3. additionadditional lithium triethylborohydride solution (10 mL) was added
  4. stirringThe reaction mixture was stirred at ambient temperature for about 1 h
  5. customthe reaction was quenched by a dropwise addition of water
  6. additionEtOAc (100 mL) was added
  7. customthe layers were separated
  8. washThe organic phase was washed with water (75 mL), IN phosphoric acid (2×100 mL)
  9. dry with materialwater (100 mL), aqueous sodium bicarbonate (100 mL) and brine (100 mL) then dried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-df450fe39c6b4524babf46b9635b3c23
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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