1,4-Dioxane → HCID 10953837, compound

HRID 2369818Notes

Reaction equation

HRID 2369818 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:12]C(=O)OC(C)(C)C)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+:2]=[N-:3].O1CCOCC1>C1COCC1.Cl.CCOCC>[N:1]([CH2:4][C@@H:5]([NH2:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[N+:2]=[N-:3]

Participants

6

Reactant 2

HCID 312751,4-DioxaneHCID 86762376HCID 86762376, compound

Product 1

HCID 10953837HCID 10953837, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [(1S)-2-azido-1-phenylethyl]carbamate (210 mg, 0.8 mmol, 1.0 eq.) in THF (2 ml), 4.0M hydrogen chloride in dioxane (2.0 ml, 8.0 mmol, 10.0 eq.) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ether. The precipitate was filtered and washed with ether to yield (S)-2-Azido-1-phenyl-ethylamine 40 as a white solid in 85% yield. LC-MS [163 (M+1)]

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ether

Sources & evidence

ORD record
ord-6028b2eaf91d40dd93fb9a8472577295
Source dataset
uspto-grants-2014_04
Patent number
US08710044B2

Reaction notes

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