Dimethyl Sulfoxide → HCID 86615381, compound

HRID 1436734Notes

Reaction equation

HRID 1436734 reaction equation
CS(C)=O.[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14][C@@H:13]1[CH2:26][OH:27])=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>>[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:15][CH2:14][C@@H:13]1[CH:26]=[O:27])=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 86615382HCID 86615382, compound

Product 1

HCID 86615381HCID 86615381, compound

Procedure

Add sulfur trioxide pyridine complex (0.27 g, 1.7 mmol) in dimethylsulfoxide (0.95 mL, 13.0 mmol) to (2R, 5R)-5-Benzyloxy-2-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (0.27 g, 0.84 mmol) in triethylamine (0.70 mL, 5.0 mmol) at 10° C. and stir at room temperature for 30 minutes. Quench with water and extract with diethyl ether. Combine the organic layers, wash with 5% aqueous citric acid followed by saturated aqueous sodium chloride, dry over magnesium sulfate and concentrate. The residue may be used without further purification.

Workup

  1. customQuench with water
  2. extractionextract with diethyl ether
  3. washwash with 5% aqueous citric acid
  4. dry with materialdry over magnesium sulfate
  5. concentrationconcentrate
  6. customThe residue may be used without further purification

Sources & evidence

ORD record
ord-ed4bd3e5e4ba49e4af7969128766be49
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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