Dichloromethane → HCID 67516105, compound

HRID 470590Notes

Reaction equation

HRID 470590 reaction equation
[N:1]([CH:4]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([C:14]3[N:18]=[C:17]([C:19]4[O:23][N:22]=[C:21]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:20]=4[C:30]([F:33])([F:32])[F:31])[O:16][N:15]=3)[CH:8]=[CH:7][C:6]=2[CH:5]1[O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[N+]=[N-].C(OCC)(=O)C.C(Cl)Cl.O.O.[Sn](Cl)Cl>CO>[Si:35]([O:34][CH:5]1[C:6]2[C:11](=[CH:10][C:9]([C:14]3[N:18]=[C:17]([C:19]4[O:23][N:22]=[C:21]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:20]=4[C:30]([F:31])([F:32])[F:33])[O:16][N:15]=3)=[CH:8][CH:7]=2)[CH2:12][CH2:13][CH:4]1[NH2:1])([C:38]([CH3:40])([CH3:41])[CH3:39])([CH3:36])[CH3:37]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 89791237HCID 89791237, compound

Product 1

HCID 67516105HCID 67516105, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Racemic 3-(6-azido-5-(tert-butyldimethylsilyloxy)-5,6,7,8-tetrahydronaphthalen-2-yl)-5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazole (500 mg, 0.86 mmol) was dissolved in MeOH (2131 μL), ethyl acetate (2131 μL), and CH2Cl2 (2131 μL). To this solution was added tin(II) chloride dihydrate (1.94 mg, 8.6 mmol) and the reaction mixture was stirred overnight. The solvent was evaporated and the residue was redissolved in CH2Cl2 and washed with 1N NaOH and brine. The organic phase was dried over MgSO4 and concentrated to afford racemic (1S*,2R*)-1-(tert-butyldimethylsilyloxy)-6-(5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-2-amine (46.2 mg, 0.83 mmol, 96.5%) as a pale yellow oil: LCMS=557.44 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was redissolved in CH2Cl2
  3. washwashed with 1N NaOH and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-55ac591fb9324b9baacccc0900a65a81
Source dataset
uspto-grants-2014_01
Patent number
US08629282B2

Reaction notes

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