Amphetamine → (2S,3Z)-1,4-Diphenylbut-3-en-2-amine

HRID 573010Notes

Reaction equation

HRID 573010 reaction equation
[OH-].[K+].BrC(Br)(F)F.[C:8]1([CH2:14][CH:15]([NH2:17])[CH3:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO.C(O)CCC>[C:8]1([CH2:14][C@H:15]([NH2:17])/[CH:16]=[CH:14]\[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 3007AmphetamineHCID 6382DibromodifluoromethaneHCID 14797Potassium Hydroxide2×

Product 1

HCID 68309515(2S,3Z)-1,4-Diphenylbut-3-en-2-amine

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 887MethanolSolvent

Procedure

552.7 mg (9.85 mmol) potassium hydroxide was dissolved in methanol, absorbed onto 1.1 g aluminum oxide and then dried in a high vacuum. At 5-10° C., 307 μL (3.3 mmol) dibromodifluoromethane was added by drops to a solution of 240 mg (0.82 mmol) (2S)-1-benzylsulfonyl)-3-phenylpropan-2-amine and 1.56 g of the potassium hydroxide prepared in this way on aluminum oxide in 6.2 mL n-butanol. The reaction mixture was stirred for two hours at RT, then filtered through Celite, and the residue was rewashed well with dichloromethane. The filtrate was concentrated and the resulting residue was dried in vacuo. The resulting raw produce was purified by preparative HPLC, yielding 98 mg (35% of the theoretical) of the title compound with an E/Z diasteromer ratio of 4:1.

Workup

  1. customabsorbed onto 1.1 g aluminum oxide
  2. customdried in a high vacuum
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe resulting residue was dried in vacuo
  6. customThe resulting raw produce
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-9d09f688c85d4315a373ece010928c43
Source dataset
uspto-grants-2015_05
Patent number
US09029406B2

Reaction notes

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