4-Fluoro-N-methyl-benzenepropanamine → (2S,3R)-3-(dibenzylamino)-1-[[3-(4-fluorophenyl)propyl](methyl)amino]butan-2-ol

HRID 1592363Notes

Reaction equation

HRID 1592363 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.[CH2:13]([N:20]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@@H:21]([C@H:23]1[CH2:25][O:24]1)[CH3:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:13]([N:20]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C@H:21]([CH3:22])[C@@H:23]([OH:24])[CH2:25][N:2]([CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=1)[CH3:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 110842664-Fluoro-N-methyl-benzenepropanamineHCID 86599637(1R)-N,N-dibenzyl-1-[(2S)-oxiran-2-yl]ethanamine

Product 1

HCID 58997715(2S,3R)-3-(dibenzylamino)-1-[[3-(4-fluorophenyl)propyl](methyl)amino]butan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The product of Step e (1.30 g, 7.80 mmol, 1 eq.), (1R)-N,N-dibenzyl-1-[(2S)-oxiran-2-yl]ethanamine (the synthesis of which is described in Example 100) (2.08 g, 7.80 mmol, 1 eq.) and ethanol (10 mL) were mixed at 25° C. under N2 then refluxed overnight. Worked up by stripping off the ethanol then purifying the residue over silica gel in 1:1 Hexanes/EtOAc to 100% EtOAc. Obtained 1.16 g of an amber oil. MS (ESI) detects (M+H)+=435.

Workup

  1. additionwere mixed at 25° C. under N2
  2. temperaturethen refluxed overnight
  3. customthen purifying the residue over silica gel in 1:1 Hexanes/EtOAc to 100% EtOAc

Sources & evidence

ORD record
ord-7e976d1233144079b6a53b4485ba0de5
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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