Borane;tetrahydrofuran → (2S,4S)-4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

HRID 1442974Notes

Reaction equation

HRID 1442974 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13](O)=[O:14])[CH2:10][CH:9]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O1CCCC1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][OH:14])[CH2:10][C@H:9]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68544941Pyrrolidine-1,2,4-tricarboxylic acid 1,2-di-tert-butyl ester

Product 1

HCID 59166759(2S,4S)-4-hydroxymethyl-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl esterYield 27.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pyrrolidine-1,2,4-tricarboxylic acid 1,2-di-tert-butyl ester (Preparation 44, 501 mg, 1.59 mmol) in anhydrous tetrahydrofuran (10 ml) at 0° C. under a nitrogen atmosphere was added borane-tetrahydrofuran complex (1M in tetrahydrofuran, 3.16 ml, 3.18 mmol) dropwise and allowed to stir to room temperature over 18 hours. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate (10 ml) and washed with 1M hydrochloric acid (10 ml), saturated sodium hydrogen carbonate (10 ml) and then dried (MgSO4), filtered and evaporated under reduced presssure to give the title compound as a colourless gum (single diastereonier 132 mg, 27%)

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate (10 ml)
  3. washwashed with 1M hydrochloric acid (10 ml), saturated sodium hydrogen carbonate (10 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced presssure

Sources & evidence

ORD record
ord-66b0a28c38ab47c0adcce9286056ef72
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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