(1R,3S,5R)-3-Azidomethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester → tert-Butyl (1R,3S,5R)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

HRID 1527444Notes

Reaction equation

HRID 1527444 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][N:15]=[N+]=[N-])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH2:15])[CH2:12][C@@H:11]2[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 86673859(1R,3S,5R)-3-Azidomethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Product 1

HCID 68284067tert-Butyl (1R,3S,5R)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1R,3S,5R)-3-azidomethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (195 mg, 0.82 mmol) was suspended in THF (10 mL). Air was removed from the flask and replaced with nitrogen three times. Pd/C 10% (20 mg) was added to the solution which was again degassed, placed under a hydrogen atmosphere, and stirred at RT overnight. The catalyst was removed through a 0.45 microns filter, and the filtrate was concentrated in vacuo to give the title compound. MS (LC-MS): 213.0 [M+H]+; tR (HPLC conditions k): 2.51 min. The material thus obtained was used in the next step without further purification.

Workup

  1. customAir was removed from the flask
  2. additionPd/C 10% (20 mg) was added to the solution which
  3. customwas again degassed
  4. customThe catalyst was removed through a 0.45 microns
  5. filtrationfilter
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-178661041c784ce9a315003460ce7df8
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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