1,4-Dioxane → (S)-1-azido-3-phenylpropan-2-amine

HRID 1254244Notes

Reaction equation

HRID 1254244 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:13]C(=O)OC(C)(C)C)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3].O1CCOCC1>Cl.C(Cl)Cl>[N:1]([CH2:4][C@@H:5]([NH2:13])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 9970678tert-butyl (S)-3-azido-1-phenylpropan-2-ylcarbamate

Product 1

HCID 11769078(S)-1-azido-3-phenylpropan-2-amineYield 128.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (S)-3-azido-1-phenylpropan-2-ylcarbamate (1.0045 g, 3.6 mmol) was dissolved in 4 M HCl in dioxane (20 mL, 80 mmol) and stirred at rt for 2 h. The solvent was stripped. The residue was taken up in CH2Cl2 (50 mL) and 1 N aq NaOH (10 mL), extracted with CH2Cl2 (3×10 mL), washed with brine (3×5 mL), dried (Na2SO4), decanted, and stripped to afford (S)-1-azido-3-phenylpropan-2-amine (812.9 mg, quant, 80% purity) as a clear oil. MS ESI +ve m/z 177 (M+1).

Workup

  1. extraction1 N aq NaOH (10 mL), extracted with CH2Cl2 (3×10 mL)
  2. washwashed with brine (3×5 mL)
  3. dry with materialdried (Na2SO4)
  4. customdecanted

Sources & evidence

ORD record
ord-9ee682cfa8264d95859782b03b2c6d63
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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