Dimethyl Sulfoxide → HCID 86630311, compound

HRID 1171601Notes

Reaction equation

HRID 1171601 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C:19]([C@H:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][C@@H:22]1[CH2:34][OH:35])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([O:18][C:19]([C@H:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH2:23][C@@H:22]1[CH:34]=[O:35])=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68764885HCID 68764885, compound

Product 1

HCID 86630311HCID 86630311, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of anhydrous DMSO (1.8 mL, 25.36 mMol) in CH2Cl2 (40 mL) at −78° C. was added oxalyl chloride (2 mL, 23.78 mMol) slowly. After 20 min, a sample of (3R,4S)-tert-butyl 4-(benzyloxycarbonyl)-3-(hydroxymethyl)piperidine-1-carboxylate (5.78 g, 15.85 mMol) dissolved in CH2Cl2 (30 mL) was added to the reaction slowly. Stirring was continued for 1 h. Triethylamine (6.6 mL, 47.55 mMol) was added dropwise. Stirring was then continued with a gradual warm up to 0° C. over 1 h. Partitioned the mixture between water and CH2Cl2. Aqueous layer was re-extracted with CH2Cl2. Combined organic layer was washed with brine and dried (Na2SO4). Filtered, concentrated and chromatographed to get the desired product, (3R,4S)-tert-butyl 4-(benzyloxycarbonyl)-3-formylpiperidine-1-carboxylate as a pale oil (3.8 g, yield=67%).

Workup

  1. additionwas added to the reaction slowly
  2. waitwas continued for 1 h
  3. stirringStirring
  4. customPartitioned the mixture between water and CH2Cl2
  5. extractionAqueous layer was re-extracted with CH2Cl2
  6. washCombined organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationFiltered
  9. concentrationconcentrated
  10. customchromatographed

Sources & evidence

ORD record
ord-3f7c2b3021d941648aa3b1e53b43dd77
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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