Sodium Bicarbonate → HCID 57240977, compound

HRID 2299673Notes

Reaction equation

HRID 2299673 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[C:17]([O:22][CH3:23])[C:18]([O:20][CH3:21])=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:24]([CH2:31][C@H:32]1[O:34][CH2:33]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([N:8]([CH2:33][C@H:32]([OH:34])[CH2:31][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[C:17]([O:22][CH3:23])[C:18]([O:20][CH3:21])=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 2733225Ytterbium triflateHCID 18007383HCID 18007383, compound

Product 1

HCID 57240977HCID 57240977, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, to a solution of N-benzyl-(2,3-dimethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl) amine (440 mg) and (2S)-1-phenoxy-2,3-epoxypropane (190 mg) in dichloromethane (10 ml) was added ytterbium(III) trifluoromethanesulfonate (157 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hours. The resulting mixture was poured into saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel to afford (2S)-1-[N-benzyl-N-(2,3-dimethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (400 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (hexane-ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-a231baf864cd48d99564daf0fbb1b362
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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