Silicon tetrachloride → 2-[3-(5-Benzyl-tetrazol-1-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester

HRID 2045486Notes

Reaction equation

HRID 2045486 reaction equation
Cl[Si](Cl)(Cl)Cl.[N-:6]=[N+:7]=[N-:8].[Na+].[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32](=O)[CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH:26]=1)[C:19]([CH3:42])([CH3:41])[CH2:18]2)=[O:14])[CH3:11]>C(#N)C>[CH2:10]([O:12][C:13]([C:15]1[CH:24]=[C:23]2[C:22](=[CH:17][CH:16]=1)[NH:21][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([N:31]3[C:32]([CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[N:8][N:7]=[N:6]3)[CH:26]=1)[C:19]([CH3:18])([CH3:42])[CH2:41]2)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 24816Silicon tetrachlorideHCID 33557Sodium AzideHCID 67443648HCID 67443648, compound

Product 1

HCID 674438922-[3-(5-Benzyl-tetrazol-1-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl esterYield 58.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of tetrachlorosilane (6.0 mL, 52 mmol), sodium azide (5.1 g, 78.1 mmol) in dry acetonitrile (20 mL) was added 3,3-dimethyl-2-(3-phenylacetylamino-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (2.3 g, 5.2 mmol) at room temperature. Then the mixture solution was stirred at room temperature for over night. LC/MS showed that reaction finished completely. The reaction mixture was poured into ice-cold saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2×200 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (40% ethyl acetate/hexanes) afforded 2-[3-(5-benzyl-tetrazol-1-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (1.4 g, 58.3%) as a white solid: LC/MS m/e calcd for C28H29N5O2 (M+H)+: 468.58, observed: 468.1.

Workup

  1. customLC/MS showed that reaction
  2. additionThe reaction mixture was poured into ice-cold saturated aqueous sodium bicarbonate solution
  3. extractionextracted with ethyl acetate (2×200 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f7182678df184acd8d134ee43fc0813e
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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