Potassium Bicarbonate → Di-tert-butyl (2s,5s)-5-hydroxyethylpyrrolidine-1,2-dicarboxylate

HRID 10420

Reaction equation

HRID 10420 reaction equation
C([O:3][C:4]([CH2:6][C@H:7]1[N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@H:10]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:9][CH2:8]1)=O)C.[BH4-].[Li+].C(=O)(O)[O-].[K+]>C(OCC)C>[OH:3][CH2:4][CH2:6][C@H:7]1[N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[C@H:10]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 4148881Lithium borohydrideHCID 91432523di-tert-butyl (2S,5S)-5-ethoxycarbonylmethylpyrrolidine-1,2-dicarboxylate

Product 1

HCID 91484630Di-tert-butyl (2s,5s)-5-hydroxyethylpyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

43 g of the product from 1d were dissolved in 300 ml of diethyl ether. A solution of 3.1 g of lithium borohydride in 300 ml of diethyl ether was added dropwise thereto. The mixture was stirred for 6 h and the reaction was stopped by cautious addition of 300 ml of a saturated potassium bicarbonate solution. The phases were separated and the organic phase was washed with 250 ml of a saturated sodium chloride solution. The organic phase was dried with sodium sulfate, and the solvent was removed in vacuo. The residue was chromatographed on silica gel.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with 250 ml of a saturated sodium chloride solution
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-2ee3358ec00f4d3a99109190e3ee13ea
Source dataset
uspto-grants-2006_08
Patent number
US07094800B2

Linked notes

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