Acetic Acid → HCID 60135625, compound

HRID 2384555Notes

Reaction equation

HRID 2384555 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][NH:11][CH2:10]3)=[CH:5][CH:4]=1.[OH:17][CH2:18][CH2:19][C:20](=O)[CH3:21].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][N:11]([CH:20]([CH3:21])[CH2:19][CH2:18][OH:17])[CH2:10]3)=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 1115094-Hydroxy-2-ButanoneHCID 5049666Sodium triacetoxyborohydrideHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Product 1

HCID 60135625HCID 60135625, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (1S,5R)-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (Preparation 18, 100 mg) in tetrahydrofuran (1.1 mL), 4-hydroxy-2-butanone (0.66 mmol), acetic acid (0.66 mmol) and NaBH(OAc)3 (0.88 mmol) were added. The mixture was stirred at room temperature for 2 h. After addition of NaOH (1M), the solvent was eliminated under vacuo, the residue was dissolved in ethyl acetate and the organic layer was washed with H2O and dried over Na2SO4. This solution was concentrated in vacuo to give 130 mg of the title compound which was used without further purification.

Workup

  1. additionwere added
  2. washthe organic layer was washed with H2O
  3. dry with materialdried over Na2SO4
  4. concentrationThis solution was concentrated in vacuo

Sources & evidence

ORD record
ord-af020452e5734430abc5889dbbf1d60f
Source dataset
uspto-grants-2012_09
Patent number
US08263782B2

Reaction notes

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