Sodium Bicarbonate → HCID 57286180, compound

HRID 1351885Notes

Reaction equation

HRID 1351885 reaction equation
Cl.[CH2:2]([NH:9][CH:10]1[CH2:16][CH2:15][CH2:14][C:13]2[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:12]=2[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:22]([CH2:29][C@H:30]1[O:32][CH2:31]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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>[CH2:2]([N:9]([CH2:31][C@H:30]([OH:32])[CH2:29][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:10]1[CH2:16][CH2:15][CH2:14][C:13]2[CH:17]=[CH:18][C:19]([OH:21])=[CH:20][C:12]=2[CH2:11]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 2733225Ytterbium triflateHCID 18007283HCID 18007283, compound

Product 1

HCID 57286180HCID 57286180, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

under nitrogen, to a solution of N-benzyl-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine hydrochloride (300 mg) and (2S)-1-phenoxy-2,3-epoxypropane (193 mg) in dichloromethane (10 ml) was added ytterbium(III) trifluoromethanesulfonate (61 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-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (340 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-9f1361dc1eb040faab08ab9346bca302
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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