Sodium Hydroxide → 7-Benzyl-1-tert-butoxycarbonylaminomethyl-2-oxa-7-azabicyclo[3.3.0]octane

HRID 53877Notes

Reaction equation

HRID 53877 reaction equation
[OH-:1].[Na+].[NH2:3][CH2:4][C:5]12[CH2:12][N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH:9]1[CH2:8][CH2:7][O:6]2>O.C(O)(C)(C)C>[CH2:13]([N:11]1[CH2:12][C:5]2([CH2:4][NH:3][C:7]([O:6][C:5]([CH3:12])([CH3:9])[CH3:4])=[O:1])[CH:9]([CH2:8][CH2:7][O:6]2)[CH2:10]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15380948HCID 15380948, compound

Product 1

HCID 217047517-Benzyl-1-tert-butoxycarbonylaminomethyl-2-oxa-7-azabicyclo[3.3.0]octane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

2 g of NaOH in 45 ml of water are added to 10.4 g (44.7 mmol) of 1-aminomethyl-7-benzyl-2-oxa-7-azabicyclo[3.3.0]octane in 56 ml of tert-butanol, and 10.2 g (47 mmol) of di-tert-butyl pyrodicarbonate are then added dropwise. The mixture is stirred at room temperature for 15 hours, and then extraction with chloroform, drying over potassium carbonate, concentration and distillation are carried out. Yield: 12.2 g (82% of theory) Boiling point: 170° C./0.15 mbar The product is 94% pure by gas chromatography.

Workup

  1. additionare then added dropwise
  2. extractionextraction with chloroform
  3. dry with materialdrying over potassium carbonate, concentration and distillation

Sources & evidence

ORD record
ord-c59503dc4a714864914894ff6abdeeeb
Source dataset
uspto-grants-1997_04
Patent number
US05621105

Reaction notes

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