Benzaldehyde → HCID 54398611, compound

HRID 274051Notes

Reaction equation

HRID 274051 reaction equation
[NH2:1][C@H:2]1[CH2:8][C:7]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H][H]>[Pd].C(OCC)(=O)C.C(O)(=O)C.C(O)C>[CH2:14]([NH:1][C@H:2]1[CH2:8][C:7]2[CH:9]=[C:10]([OH:13])[CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][CH2:3]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 3

HCID 240Benzaldehyde2×HCID 54435238HCID 54435238, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54398611HCID 54398611, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-8-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (5.8 g; contaminated with ammonium bromide), benzaldehyde (5.3 ml), acetic acid (0.15 ml), 10% palladium on carbon (50% wet; 1.1 g), and ethanol (260 ml) was stirred under hydrogen for 1 hour, and then an additional portion of benzaldehyde (5.3 ml) was added. After aging for 0.5 hour, hydrogen was introduced to the reaction mixture and stirring was continued for an additional 3 hours. To the reaction mixture was added an additional portion of acetic acid (0.15 ml), and the mixture was stirred under 1 atm of hydrogen for an additional 1 hour. The catalyst was filtered off, and washed with ethanol. Removal of the solvent in vacuo afforded the residue, which was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; chloroform, then 100:1 to 50:1 to 10:1 chloroform-methanol) to give (R)-8-benzylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ol (6.6 g). Physical data are shown for the hydrochloride of the product, which was recrystallized from 3:1 diisopropyl ether-ethanol.

Workup

  1. waitAfter aging for 0.5 hour
  2. stirringstirring
  3. waitwas continued for an additional 3 hours
  4. filtrationThe catalyst was filtered off
  5. washwashed with ethanol
  6. customRemoval of the solvent in vacuo
  7. customafforded the residue, which
  8. washwashed with saturated aqueous sodium bicarbonate and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by column chromatography on silica gel (
  12. washgradient elution

Sources & evidence

ORD record
ord-6fcd985006d64f5cb9b4bfb9cab8b995
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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