1-(Phenyl(tetrahydrofuran-2-yl)methyl)urea → 1-((S)-phenyl((S)-tetrahydrofuran-2-yl)methyl)urea

HRID 590786Notes

Reaction equation

HRID 590786 reaction equation
[C:1]1([CH:7]([CH:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[NH:8][C:9]([NH2:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO>[C:1]1([C@@H:7]([C@@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[NH:8][C:9]([NH2:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 1182717571-(Phenyl(tetrahydrofuran-2-yl)methyl)urea

Product 1

HCID 1182724151-((S)-phenyl((S)-tetrahydrofuran-2-yl)methyl)urea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The enantiomers of 1-(phenyl(tetrahydrofuran-2-yl)methyl)urea (150 mg, 0.681 mmol) were separated by SFC (Berger Multigram II, Column: Chiral Technology OZ-H 2.1×25 cm, SuM, UV wavelength: 220 nM, mobile phase: 40%/60% Methanol+0.25% dimethyl ethylamine/CO2(1), flow rate: 70 mL/Min, 7 min run time). Elution was observed at 2.46 min. The fractions were collected and the solvent evaporated in vacuo to afford 1-((S)-phenyl((S)-tetrahydrofuran-2-yl)methyl)urea and Intermediates 149A-151A. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 7.23 (m, 4H), 7.18 (m, 1H), 6.43 (d, J=9.5, 1H), 5.57 (br s, 2H), 4.68-4.47 (dd, J=3.5, J=5.5, 1H), 3.97 (m, 1H), 3.76 (q, J=8.0 1H), 3.56 (q, J=7.0, 1H), 1.79-1.75 (m, 3H), 1.73 (m, 1H).

Workup

  1. washElution
  2. customThe fractions were collected
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-b44b0cee104a43a0a9b23c41b3e50468
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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