Hydrochloric Acid → (1R*,3R*,4R*)-4-Azido-3-methylcyclohexanamine hydrochloride

HRID 2208149Notes

Reaction equation

HRID 2208149 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([NH:10]C(=O)OC(C)(C)C)[CH2:6][C@H:5]1[CH3:18])=[N+:2]=[N-:3].[ClH:19].C(OC)(C)(C)C>C1COCC1>[ClH:19].[N:1]([C@@H:4]1[CH2:9][CH2:8][C@@H:7]([NH2:10])[CH2:6][C@H:5]1[CH3:18])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 131732233tert-Butyl[(1R*,3R*,4R*)-4-azido-3-methylcyclohexyl]carbamate

Product 1

HCID 86666642(1R*,3R*,4R*)-4-Azido-3-methylcyclohexanamine hydrochlorideYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl [(1R*,3R*,4R*)-4-azido-3-methylcyclohexyl]carbamate (example C10; 2.5 g; 10.0 mmol) is dissolved in THF (25.0 mL). After addition of HCl (4M solution in dioxane; 10.0 mL; 40.0 mmol) the reaction mixture is stirred at ambient temperature over night and gently refluxed for additional 6 hours. tert-BuOMe is added at ambient temperature, the precipitated product is collected by suction filtration, washed with several small portions of tert-BuOMe and dried under reduced pressure to yield 1.8 g of the title compound as colourless solid.

Workup

  1. temperaturegently refluxed for additional 6 hours
  2. filtrationthe precipitated product is collected by suction filtration
  3. washwashed with several small portions of tert-BuOMe
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-1dc9f71dd3c0416dac8acae0cf1f3932
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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