Water → HCID 66848259, compound

HRID 1625520Notes

Reaction equation

HRID 1625520 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH3:13])[CH2:10][C@H:9]1[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.[NH4+].[Cl-].O>C1COCC1>[OH:15][CH2:14][C@@H:9]1[CH2:10][CH:11]([CH3:13])[CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6331BoraneHCID 25517Ammonium ChlorideHCID 66990176HCID 66990176, compound

Product 1

HCID 66848259HCID 66848259, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2S)-1-tert-butoxycarbonyl-4-methyl-pyrrolidine-2-carboxylic acid (26.6 g, 116.0 mmol) in THF (160 mL) is added 1 M borane in THF (243.6 mL, 243.6 mmol) at 0° C. The reaction mixture is stirred at rt overnight. Then a saturated aqueous solution of NH4Cl (50 mL) is carefully added (dropwise) at 4° C., followed by H2O (100 mL). The mixture is extracted with EtOAc and the organic phase is washed with H2O, dried over Na2SO4, filtered and concentrated to dryness. The residue is purified by flash column chromatography on silica gel (0 to 20% EtOAc in Hexanes) to give tert-butyl (2S)-2-(hydroxymethyl)-4-methyl-pyrrolidine-1-carboxylate (23.5 g, 94%).

Workup

  1. extractionThe mixture is extracted with EtOAc
  2. washthe organic phase is washed with H2O
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by flash column chromatography on silica gel (0 to 20% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-fb0991d28c5d447d8af7f065d4a2e337
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

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