HCID 10669852, compound → HCID 10717063, compound

HRID 2258353Notes

Reaction equation

HRID 2258353 reaction equation
[CH2:1]([N:4]1[C@H:9]([CH3:10])[CH2:8][N:7]([C@@H:11]([C:19]2[S:20][CH:21]=[C:22]([Br:24])[CH:23]=2)[C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)[C@@H:6]([CH3:25])[CH2:5]1)[CH:2]=[CH2:3]>C(O)C>[CH2:1]([N:4]1[C@@H:9]([CH3:10])[CH2:8][N:7]([C@H:11]([C:19]2[S:20][CH:21]=[C:22]([Br:24])[CH:23]=2)[C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)[C@H:6]([CH3:25])[CH2:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 10669852HCID 10669852, compound

Product 1

HCID 10717063HCID 10717063, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4.22 g (11 mmol) of (-)-p-ditoluoyl-L-tartaric acid in 15 mL of absolute ethanol was added to a suspension of 2.3 g (5.5 mmol) of (±)-3-((R*)-((2S*,5R*)-4-allyl-2,5-dimethyl-1-piperazinyl)(4-bromo-2-thienyl)-methyl)phenol (Example 42) in 5 mL of absolute ethanol. The mixture was heated to boiling and the resulting clear solution was allowed to crystallize at room temperature. After three crystallizations, the salt was converted to the free amine as in Example 65 and recrystallized from absolute ethanol to give 0.490 g (43% of theoretical for one enantiomer) of (+)-3-((S)-((2R,5S)-4-allyl-2,5-dimethyl-1-piperazinyl)(4-bromo-2-thienyl)methyl)phenol as white crystals, mp 183°-185° C. Absolute configuration was determined by x-ray crystallography. [α]D20 =+14.5° (tetrahydrofuran, c=3.3). HPLC on β-cyclodextrin with methanol: 0.1M ammonium acetate/1:1 gave one peak at tR =11 min. Calc. for C20H25BrN2OS: C, 57.00; H, 5.98; N, 6.65; Br, 18.96; S, 7.61. Found: C, 56.93; H, 5.99; N, 6.67; Br, 19.04; S, 7.67.

Workup

  1. temperatureThe mixture was heated
  2. customto crystallize at room temperature
  3. customAfter three crystallizations
  4. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-b3caafe88df043e8b0735b12c2f7d8fd
Source dataset
uspto-grants-1997_08
Patent number
US05658908

Reaction notes

Loading…