Acetic Acid → HCID 118324755, compound

HRID 587853Notes

Reaction equation

HRID 587853 reaction equation
[C:1]1([C@H:11]([NH2:13])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=O.C(O)(=O)C.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO.O>[C:1]1([C@H:11]([NH:13][CH:20]2[CH2:21][CH2:22][C:23]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 682662-TetraloneHCID 516892Sodium BicarbonateHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 118324755HCID 118324755, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of (R)-1-(naphthalen-1-yl)ethanamine (4.77 ml, 29.5 mmol) in methanol (50 mL) was added 3,4-dihydronaphthalen-2(1H)-one (4.80 g, 32.8 mmol) at 0° C. Acetic acid (2.349 mL, 41.0 mmol) was added and the reaction was stirred for 5 min. After that the reaction was warmed to RT and further stirred for 20 minutes. Again reaction was cooled to 0° C. and sodium cyanoborohydride (3.09 g, 49.2 mmol) was added stirred overnight at RT. After completion of reaction, —NaHCO3 solution (20 mL) and water (50 mL) were added and the mixture was extracted with ethyl acetate (50 mL×2). The extract was washed with saturated brine, dried over anhydrous Na2SO4 and evaporated under reduced pressure to get the crude compound. This was used directly in the next reaction (11.1 g, 36.8 mmol); m/z 302.65.

Workup

  1. stirringfurther stirred for 20 minutes
  2. customAgain reaction
  3. temperaturewas cooled to 0° C.
  4. stirringstirred overnight at RT
  5. customAfter completion of reaction
  6. extractionthe mixture was extracted with ethyl acetate (50 mL×2)
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0170deeb1430451e9b0356603efe64de
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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