Sodium Bicarbonate → HCID 57284591, compound

HRID 2299669Notes

Reaction equation

HRID 2299669 reaction equation
[CH2:1]([N:8]([CH:20]1[CH2:26][C:25]2[CH:27]=[C:28]([C:31]([NH2:33])=O)[CH:29]=[CH:30][C:24]=2[CH2:23][CH2:22][CH2:21]1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+]>O1CCCC1>[NH2:33][CH2:31][C:28]1[CH:29]=[CH:30][C:24]2[CH2:23][CH2:22][CH2:21][CH:20]([N:8]([CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:26][C:25]=2[CH:27]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 57120988HCID 57120988, compound

Product 1

HCID 57284591HCID 57284591, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxamide (3.00 g) in dry tetrahydrofuran (90 ml) was gradually added lithium aluminum hydride (1.02 g) under ice-cooling and nitrogen atmosphere. The mixture was then heated to reflux for 3 hours. Saturated sodium bicarbonate solution was added dropwise to the reaction mixture under ice-cooling, and the resulting precipitate was filtered off and washed with ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (30:1 to 5:1) to afford (2S)-1-[N-(3-aminomethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-benzylamino]-3-phenoxy-2-propanol (2.75 g).

Workup

  1. temperaturecooling
  2. temperatureThe mixture was then heated
  3. temperatureto reflux for 3 hours
  4. temperaturecooling
  5. filtrationthe resulting precipitate was filtered off
  6. washwashed with ethyl acetate
  7. extractionThe filtrate was extracted with ethyl acetate
  8. washthe organic layer was washed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (30:1 to 5:1)

Sources & evidence

ORD record
ord-d8b1bb6ef1504fc79454f43a66c9c2e7
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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