Acetic Acid → HCID 118324845, compound

HRID 587859Notes

Reaction equation

HRID 587859 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@H:12]([NH2:14])[CH3:13])=[CH:4][CH:3]=1.[O:15]=[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][C@@H:18]([CH2:26][CH:27]=O)[CH2:17]1.C(O)(=O)C.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO.O>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C@H:12]([NH:14][CH2:27][CH2:26][C@@H:18]2[CH2:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:16](=[O:15])[CH2:17]2)[CH3:13])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 55278857HCID 55278857, compoundHCID 90003554HCID 90003554, compound

Product 1

HCID 118324845HCID 118324845, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of (R)-1-(4-fluoronaphthalen-1-yl)ethanamine (1.206 g, 6.38 mmol) in methanol (5 mL) was added (S)-2-(4-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetaldehyde (1.2 g, 6.38 mmol) at 0° C. Acetic acid (0.365 mL, 6.38 mmol) was added and reaction was stirred for 5 min. Reaction was warmed to RT and stirred for 20 min. Again reaction was cooled to 0° C. Sodium cyanoborohydride (0.401 g, 6.38 mmol) was added to the reaction mixture and stirred for overnight (16 h). To the reaction solution were added NaHCO3 solution (5 mL) and water (10 mL) and the mixture was extracted with ethyl acetate (20 mL×2). The extract was washed with saturated brine solution, dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude title compound (2.0 g, 5.53 mmol, 87% yield).

Workup

  1. customreaction
  2. customReaction
  3. stirringstirred for 20 min
  4. customAgain reaction
  5. temperaturewas cooled to 0° C
  6. stirringstirred for overnight (16 h)
  7. extractionthe mixture was extracted with ethyl acetate (20 mL×2)
  8. washThe extract was washed with saturated brine solution
  9. dry with materialdried over anhydrous Na2SO4
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c591aff562054644b82c696dacac2ca6
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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