Acetic Acid → HCID 67326287, compound

HRID 871871Notes

Reaction equation

HRID 871871 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH:18]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].C(O)(=O)C.[F:23][C:24]([F:29])([F:28])[CH2:25][CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O.[OH-].[Na+]>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH2:18][CH2:17][N:16]([CH2:26][CH2:25][C:24]([F:29])([F:28])[F:23])[CH2:15][CH:14]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 680283,3,3-TrifluoropropanalHCID 5049666Sodium triacetoxyborohydrideHCID 574161654-(3-Methoxy-4-nitrophenyl)-1,2,3,6-tetrahydropyridine--hydrogen chloride (1/1)

Product 1

HCID 67326287HCID 67326287, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 6.6 g (24.38 mmol) of the hydrochloride prepared in step 16.1 in 110 mL of dichloromethane is cooled in an ice-water bath. 14 mL (243.8 mmol) of glacial acetic acid, 8.19 g (73.14 mmol) of 3,3,3-trifluoropropionaldehyde and 12.9 g (60.95 mmol) of sodium triacetoxyborohydride are successively added portionwise. The mixture is stirred at room temperature for 3 hours and then diluted with dichloromethane, water and aqueous 1N NaOH solution. The aqueous phase is extracted with dichloromethane and the organic phases are combined, dried over Na2SO4, filtered and concentrated under vacuum. 8.4 g of a yellow oil very predominantly containing the expected product are recovered, and are used as obtained in the following step. Quantitative crude yield.

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. addition8.4 g of a yellow oil very predominantly containing the expected product
  6. customare recovered
  7. customas obtained in the following step
  8. customQuantitative crude yield

Sources & evidence

ORD record
ord-f6a12ddba1564f9fbe38a239ec510d89
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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