Diethyl Ether → (R)-2-azido-1-benzylethylamine

HRID 1271773Notes

Reaction equation

HRID 1271773 reaction equation
[N:1]([CH2:4][C@H:5]([NH:13]C(OC(C)(C)C)=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[N+:2]=[N-:3].CCOCC.[Na+].[Cl-]>Cl.C(O)C.O>[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

7

Reactant 3

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 229417321-azido-2-(R)-(BOC-amino)-3-phenylpropane

Product 1

HCID 14802497(R)-2-azido-1-benzylethylamineYield 78.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The compound from step 164c (4.3 g, 15.6 mmol) was dissolved in 30 mL of 4N HCl in ethanol, and the reaction mixture was stirred for 1.5 hours at room temperature. The solvent was stripped and chased with ether. The residue was dissolved in water, NaCl was added, and the mixture was extracted with ethyl ether, which was discarded. The aqueous layer was adjusted to pH 12 with K2CO3, saturated with NaCl, then extracted with CHCl3. The organic extract was washed with brine, dried (Na2SO4) and filtered. The solvent was removed under vacuum to afford 2.17 g of the title compound. MS m/z (M+H)+: 177, MS m/z (M+NH4)+: 194.

Workup

  1. extractionthe mixture was extracted with ethyl ether, which
  2. extractionextracted with CHCl3
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-8f0cf0d2871741dfa8f6dc244e7c284f
Source dataset
uspto-grants-2007_04
Patent number
USRE039591E1

Reaction notes

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