Acetic Acid → HCID 15680293, compound

HRID 2279515Notes

Reaction equation

HRID 2279515 reaction equation
[C:1]1([CH2:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][CH2:10][C:11](=O)[CH3:12].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>O.ClCCCl>[CH2:7]([NH:8][CH:11]([CH3:12])[CH2:10][F:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 9889FluoroacetoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 15680293HCID 15680293, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of phenylmethanamine (5.63 g, 52.6 mmol) and 1-fluoropropan-2-one (4.0 g, 52.6 mmol) and DCE (50 mL) was added NaBH(OAc)3 (15.6 g, 73.6 mmol) and HOAc (3.01 mL, 52.6 mmol) and the reaction was capped and stirred at RT for 3 h. The reaction was then poured into water, and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:5 to 500:10) to afford 6.2 g (70.5%) of N-benzyl-1-fluoropropan-2-amine (230).

Workup

  1. customthe reaction was capped
  2. extractionextracted with DCM
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with a DCM/MeOH gradient (500:5 to 500:10)

Sources & evidence

ORD record
ord-029096a12d934e478c904aa4fb12d25d
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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