(2S)-2-(phenoxymethyl)oxirane → HCID 57019958, compound

HRID 2299657Notes

Reaction equation

HRID 2299657 reaction equation
Cl.[CH2:2]([NH:9][CH:10]1[CH2:16][CH2:15][CH2:14][C:13]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:12]=2[CH2:11]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:23]([CH2:30][C@H:31]1[O:33][CH2:32]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(NC1CCCC2C=C(OC)C=CC=2C1)C1C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C1(C)C=CC=CC=1>[CH2:2]([N:9]([CH2:32][C@H:31]([OH:33])[CH2:30][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:10]1[CH2:16][CH2:15][CH2:14][C:13]2[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[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 1534345(2S)-2-(phenoxymethyl)oxiraneHCID 2733225Ytterbium triflateHCID 18007141Benzyl-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-amineHCID 18007433HCID 18007433, compound

Product 1

HCID 57019958HCID 57019958, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-Benzyl-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine hydrochloride was converted to the corresponding free base in a usual manner. A mixture of (2S)-3-phenoxy-1,2-epoxypropane (75 mg), N-benzyl-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl) amine (140 mg), and ytterbium(III) trifluoromethanesulfonate (93 mg) in toluene (2.6 ml) was stirred at room temperature for 3 days and partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer was separated, washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue was chromatographed (dichloromethane-methanol) over silica gel to afford (2S)-1-[N-benzyl-N-(2-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (200 mg).

Workup

  1. custompartitioned between ethyl acetate and aqueous sodium bicarbonate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed (dichloromethane-methanol) over silica gel

Sources & evidence

ORD record
ord-8fbd43094a1d4405b72da5874af65aae
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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