Thionyl Chloride → HCID 66885565, compound

HRID 1863972Notes

Reaction equation

HRID 1863972 reaction equation
S(Cl)(Cl)=O.[CH2:5]([N:12]1[CH2:17][CH2:16][C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][O:26][CH2:27][C@@H:28]([CH3:32])[CH2:29][O:30][CH3:31])=[CH:21][CH:20]=2)(O)[CH:14]([CH2:33][O:34][C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1>[CH2:5]([N:12]1[CH2:17][CH:16]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][O:26][CH2:27][C@@H:28]([CH3:32])[CH2:29][O:30][CH3:31])=[CH:21][CH:20]=2)[CH:14]([CH2:33][O:34][C:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:13]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66886139HCID 66886139, compound

Product 1

HCID 66885565HCID 66885565, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

102.636 mmol of thionyl chloride are slowly added to a solution of 85.53 mmol of 1-benzyl-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-3-(R,S)-trityloxymethyl -piperidin-4-(R,S)-ol in 250 ml of pyridine at 0° C., taking care that the internal temperature stays below 10° C. After 5 minutes, the reaction mixture is quenched by adding 50 ml of 4N NaOH solution and concentrated under reduced pressure. The residue is dissolved in ethyl acetate and washed successively with saturated aqueous sodium bicarbonate solution, water and brine, dried with sodium sulfate and evaporated. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound as a yellow oil. Rf=0.28 (EtOAc-heptane-25% ammonia conc. 100:200:1); Rt=5.64 (gradient I).

Workup

  1. customstays below 10° C
  2. customthe reaction mixture is quenched
  3. additionby adding 50 ml of 4N NaOH solution
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed successively with saturated aqueous sodium bicarbonate solution, water and brine
  7. dry with materialdried with sodium sulfate
  8. customevaporated
  9. customThe residue is purified by flash chromatography (SiO2 60F)

Sources & evidence

ORD record
ord-4f502b272b204bd0aeea92960d7468d8
Source dataset
uspto-grants-2009_12
Patent number
US07625893B2

Reaction notes

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