Methylamine → (4S)-4-(3,4-dichlorophenyl)-2-(1-(methylamino)ethyl)-1,2,3,4tetrahydronaphthalen-1-ol

HRID 556160Notes

Reaction equation

HRID 556160 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])/[C:11](=[CH:20]/[CH3:21])/[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:22][NH2:23].[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]([OH:19])[CH:11]([CH:20]([NH:23][CH3:22])[CH3:21])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 58950737(S,E)-4-(3,4-dichlorophenyl)-2-ethylidene-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 58950728(4S)-4-(3,4-dichlorophenyl)-2-(1-(methylamino)ethyl)-1,2,3,4tetrahydronaphthalen-1-olYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 42 (0.80 g, 2.52 mmol) in THF (10 mL) at ambient temperature was added methylamine solution (2.0 M in THF, 3.78 mL, 7.56 mmol). The reaction mixture was stirred for 4 h before NaBH4 (0.44 g, 11.49) was added. The reaction mixture was stirred for 3 h before being quenched by a saturated solution of NH4Cl (10 mL). The product was extracted with diethyl ether, dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane/0.1% DEA=1 :7 to 1:5) to give (4S)-4-(3,4-dichlorophenyl)-2-(1-(methylamino)ethyl)-1,2,3,4-tetrahydronaphthalen-1-ol (44) (493 mg, 56%).

Workup

  1. additionwas added
  2. custombefore being quenched by a saturated solution of NH4Cl (10 mL)
  3. extractionThe product was extracted with diethyl ether
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane/0.1% DEA=1 :7 to 1:5)

Sources & evidence

ORD record
ord-911d3b112f2f428aa9ba346fa77dba20
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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