Lithium Hydroxide → Tert-butyl (3R,4R)-3-azido-4-hydroxypyrrolidine-1-carboxylate

HRID 1952436Notes

Reaction equation

HRID 1952436 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([O:13]C(=O)C)[C@H:10]([N:17]=[N+:18]=[N-:19])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[OH-]>C1COCC1.CO>[C:1]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([N:17]=[N+:18]=[N-:19])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71682605HCID 71682605, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of (3R,4R)—N-Boc-3-azido-4-acetoxypyrrolidine (1.0 g, 3.4 mmol) in THF-MeOH (3:1, 8 mL) at 0° C. was added 1N LiOH (4 mL) dropwise. The reaction mixture was stirred at room temperature overnight, then it was evaporated under reduced pressure. Ethyl acetate (20 mL) was added to the residue and the solution was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash column (50% ethyl acetate in hexane) to give (3R,4R)—N-Boc-3-azido-4-hydroxypyrrolidine: 1H NMR (300 MHz, CDCl3) identical to that of the (3S,4S) isomer; [α]20D=−26.8° (c=1.0, CHCl3).

Workup

  1. customit was evaporated under reduced pressure
  2. additionEthyl acetate (20 mL) was added to the residue
  3. washthe solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash column (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bc4a51d3a45a4789a5b182856a2b03b7
Source dataset
uspto-grants-2013_03
Patent number
US08404866B2

Reaction notes

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