Hydrochloric Acid → (3S,4S)-4-azidotetrahydropyran-3-amine

HRID 56399Notes

Reaction equation

HRID 56399 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][O:7][CH2:6][C@H:5]1[NH:10]C(=O)OC(C)(C)C)=[N+:2]=[N-:3].O1CCOCC1.Cl.Cl>C(Cl)Cl>[N:1]([C@H:4]1[CH2:9][CH2:8][O:7][CH2:6][C@H:5]1[NH2:10])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 204431481,4-Dioxane hydrochlorideHCID 118041477tert-butyl ((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)carbamate

Product 1

HCID 118036570(3S,4S)-4-azidotetrahydropyran-3-amineYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl ((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)carbamate (1.5 g, 6.19 mmol) was taken up in DCM (5 ml) and 4N HCl dioxane (4.64 ml, 18.57 mmol) added. The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed to give (3S,4S)-4-azidotetrahydro-2H-pyran-3-amine (1.1 g, 6.16 mmol, 99% yield) as an HCl salt. MS (ES+) C5H10N4O requires: 142, found: 143 [M+H]+.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-abb8f001b85c4088b80703f312b18e0e
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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