Water → (S)-1-(3-Tert-butyloxycarbonylphenyl)-1-azidoethane

HRID 2300772Notes

Reaction equation

HRID 2300772 reaction equation
CS(O[C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=1)[CH3:7])(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+].O>CN(C)C=O>[C:17]([O:16][C:14]([C:10]1[CH:9]=[C:8]([C@@H:6]([N:21]=[N+:22]=[N-:23])[CH3:7])[CH:13]=[CH:12][CH:11]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86758754(R)-1-(3-Tert-butyloxycarbonylphenyl)ethylmethanesulfonyl Ether

Product 1

HCID 86758755(S)-1-(3-Tert-butyloxycarbonylphenyl)-1-azidoethaneYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-1-(3-tert-butyloxycarbonylphenyl)-ethyl methanesulfonyl ether (3.28 mmol) was dissolved in N,N-dimethylformamide (20 mL) and sodium azide (8.57 mmol) was added. The resultant mixture was heated to 60° C. for 45 min then stirred at room temperature overnight. Worked up by pouring into water and extracting 3× with diethyl ether. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated under reduced pressure to yield 769 mg of an oil which was used without further purification. 1H NMR (500 MHz, CDCl3): δ 7.96 (m, 2H); 7.52 (m, 1H); 7.45 (m, 1H); 4.69 (q, J=6.9 Hz, 1H): 1.63 (s, 9H); 1.57 (d, J=6.8 Hz, 3H).

Workup

  1. extractionextracting 3× with diethyl ether
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dceffdc4d38944dc903a4b835fa88925
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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