Ethanolamine → HCID 54078833, compound

HRID 1379555Notes

Reaction equation

HRID 1379555 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:2]=[CH2:3].B1C2CCC[CH:11]1CCC2.Br[C:20]1[CH:35]=[CH:34][C:23]2[C@:24]3([CH3:33])[C@@H:29]([CH2:30][CH2:31][C:22]=2[CH:21]=1)[NH:28][C:27](=[O:32])[CH2:26][CH2:25]3.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+].C(CN)O>C1COCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[CH3:11][N:28]1[C@H:29]2[C@@:24]([CH3:33])([C:23]3[CH:34]=[CH:35][C:20]([CH2:3][CH2:2][CH2:1][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)=[CH:21][C:22]=3[CH2:31][CH2:30]2)[CH2:25][CH2:26][C:27]1=[O:32]

Participants

10

Reactant 6

HCID 700EthanolamineHCID 9309AllylbenzeneHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 11119935HCID 11119935, compound

Product 1

HCID 54078833HCID 54078833, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of allylbenzene (106 mg, 0.89 mmol) in 0.5 mL of THF was added 9-BBN (0.89 mmol, 1 equiv) in THF, at 0°. Let stir for 1 h, warming to 5°. To the mixture was added (+)-(4aR)-(10bR)-8-bromo-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (250 mg, 0.812 mmol), triphenyl phosphine (42 mg, 0.16 equiv.), tetrakis(triphenylphosphine) palladium(0) (19 mg, 0.02 equiv.), 1 mL of 3N sodium hydroxide solution and an additional 1 mL of THF. The resulting mixture was heated at 80° for 18 h, cooled, and ethanolamine was added, followed by ethyl acetate. The resulting organic phase was washed with brine, dried over sodium sulfate, concentrated, and purified by silica gel chromatography (50-100% ethyl acetate/hexanes eluent gradient) to give 160 mg (59%) of the title compound as an oil. FDMS m/e=347.

Workup

  1. customat 0°
  2. temperaturewarming to 5°
  3. temperatureThe resulting mixture was heated at 80° for 18 h
  4. temperaturecooled
  5. washThe resulting organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (50-100% ethyl acetate/hexanes eluent gradient)

Sources & evidence

ORD record
ord-87e797fa6f354fb189870c39341481ca
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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