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

HRID 928190Notes

Reaction equation

HRID 928190 reaction equation
[CH:1]12[O:6][CH:5]1[CH2:4][N:3]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2]2.[N-:14]=[N+:15]=[N-:16].[Na+].[NH4+].[Cl-].[OH-].[Na+]>CO.O>[N:14]([C@H:1]1[C@H:5]([OH:6])[CH2:4][N:3]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2]1)=[N+:15]=[N-:16]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 10103880tert-Butyl 6-Oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of tert-butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (110 g, 0.595 mol) in MeOH/water (1200 mL/200 mL) were added NaN3 (77.6 g, 1.19 mol) and NH4Cl (32 g, 0.598 mol). The resulting mixture was stirred at 60° C. overnight. NaOH (0.5 N, 200 mL) was added and the mixture was concentrated to remove MeOH. The residue was extracted with CH2Cl2 (3×400 mL) and the combined organic extracts were washed with water, brine, dried over Na2SO4, and then concentrated to give the title compound as a yellow liquid (quantitative yield). Used as is in next step.

Workup

  1. concentrationthe mixture was concentrated
  2. customto remove MeOH
  3. extractionThe residue was extracted with CH2Cl2 (3×400 mL)
  4. washthe combined organic extracts were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-64df1225abc8494e8fc18bdd5cc99b19
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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