Tert-butyl (3R,4R)-3-azido-4-hydroxypyrrolidine-1-carboxylate → (3R,4R)-3-Amino-1-Boc-4-hydroxypyrrolidine

HRID 2353438Notes

Reaction equation

HRID 2353438 reaction equation
[N:1]([C@H:4]1[C@H:8]([OH:9])[CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][C@H:4]1[C@H:8]([OH:9])[CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1

Participants

4

Reactant 1

HCID 15855750Tert-butyl (3R,4R)-3-azido-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 11275699(3R,4R)-3-Amino-1-Boc-4-hydroxypyrrolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 8.0 g (35 mmol) of tert-butyl trans-3-azido-4-hydroxypyrrolidine-1-carboxylate (the compound from Step A of Intermediate 11) in 117 mL of ethanol was added 500 mg of 10% palladium on carbon. The reaction mixture was purged with hydrogen gas and held under 1 atmosphere of hydrogen for 40 h. The mixture was filtered through a pad of Celite and the filter cake was successively washed with three portions of 100 mL of methanol. The combined filtrate and washings were concentrated and used without further purification. LC/MS 103 (M+1-100).

Workup

  1. customThe reaction mixture was purged with hydrogen gas
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washthe filter cake was successively washed with three portions of 100 mL of methanol
  4. concentrationThe combined filtrate and washings were concentrated
  5. customused without further purification

Sources & evidence

ORD record
ord-b3060665f0294bfd91356332e4c5306f
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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