Ethanolamine → HCID 53791262, compound

HRID 1780512Notes

Reaction equation

HRID 1780512 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=[CH2:2].B1[CH:18]2[CH2:19][CH2:20][CH2:21][CH:14]1[CH2:15][CH2:16][CH2:17]2.C1(P([C:35]2[CH:40]=[CH:39]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+].C([CH2:45][NH2:46])O.[CH2:47]1C[O:50][CH2:49][CH2:48]1>[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>[CH3:45][N:46]1[C@H:17]2[C@@:16]([CH3:15])([C:39]3[CH:40]=[CH:35][C:14]([CH2:2][CH2:1][C:3]4[CH:12]=[CH:11][C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=4)=[CH:21][C:20]=3[CH2:19][CH2:18]2)[CH2:47][CH2:48][C:49]1=[O:50]

Participants

9

Reactant 6

HCID 700EthanolamineHCID 8028Tetrahydrofuran2×HCID 11776TriphenylphosphineHCID 132302-VinylnaphthaleneHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonane

Product 1

HCID 53791262HCID 53791262, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-vinylnaphthalene (138 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)-4-H-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 THE. 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 186 mg (60%) of the title compound as a tan solid. mp 109°-110°. FDMS m/e=383. α[D]589 =+46.45 (c=0.66, chloroform).

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-4094d98905c64b9fbf1194b4713d8552
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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