[3-(4-Fluorophenyl)propyl](2,2,2-trifluoroethyl)amine → (2S,3R)-3-(dibenzylamino)-1-[[3-(4-fluorophenyl)propyl](2,2,2-trifluoroethyl)amino]butan-2-ol

HRID 1592358Notes

Reaction equation

HRID 1592358 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:4][CH:3]=1.[CH2:17]([N:24]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@@H:25]([C@H:27]1[CH2:29][O:28]1)[CH3:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[CH2:30]([N:24]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C@H:25]([CH3:26])[C@@H:27]([OH:28])[CH2:29][N:11]([CH2:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:12][C:13]([F:14])([F:15])[F:16])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 58997685[3-(4-Fluorophenyl)propyl](2,2,2-trifluoroethyl)amineHCID 86599637(1R)-N,N-dibenzyl-1-[(2S)-oxiran-2-yl]ethanamine

Product 1

HCID 58997639(2S,3R)-3-(dibenzylamino)-1-[[3-(4-fluorophenyl)propyl](2,2,2-trifluoroethyl)amino]butan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The product of Step c (3.48 g, 15.0 mmol, 1 eq.), (1R)-N,N-dibenzyl-1-[(2S)-oxiran-2-yl]ethanamine (the synthesis of which is described in Example 100) (3.96 g, 15.0 mmol, 1 eq.) and ethanol (20 mL) were mixed at 25° C. under N2 then refluxed for 4 days. Worked up by stripping off the ethanol then purifying the residue by flash chromatography in 3:1 Hexanes/EtOAc. Obtained to 3.78 g of a yellow oil. By NMR, the oil is product and some minor impurities and was carried on to the next step. MS (ESI) detects (M+H)+=503.

Workup

  1. additionwere mixed at 25° C. under N2
  2. temperaturethen refluxed for 4 days
  3. customthen purifying the residue by flash chromatography in 3:1 Hexanes/EtOAc

Sources & evidence

ORD record
ord-0728788d435246d390e2c1ab0c2e8ae6
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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