Triethylamine → HCID 86614998, compound

HRID 732377Notes

Reaction equation

HRID 732377 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:19][C@H:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][C@@H:16]1[CH2:28][OH:29])=[O:14])([CH3:11])([CH3:10])[CH3:9]>CS(C)=O.C(OCC)C>[C:8]([O:12][C:13]([N:15]1[CH2:19][C@H:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:17][C@@H:16]1[CH:28]=[O:29])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 688152181,1-Dimethylethyl (2R,4R)-2-(hydroxymethyl)-4-(phenylmethoxy)-1-pyrrolidinecarboxylate

Product 1

HCID 86614998HCID 86614998, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

Add triethylamine (1.1 mL, 7.79 mmol) and sulfurtrioxide-pyridine complex (0.63 g, 3.89 mmol) to an ice cold solution of (2R,4R)-4-benzyloxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.6 g, 1.95 mmol) in dimethyl sulfoxide (2 mL). Stir 30 minutes, warm to room temperature and stir 30 minutes. Dilute with ethyl ether and wash with 5% aqueous citric acid (3×120 mL), saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title compound as an oil (0.59 g, 100%).

Workup

  1. stirringstir 30 minutes
  2. washwash with 5% aqueous citric acid (3×120 mL), saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-b6ae2f34caee41cba02708fb0147d7c8
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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