4-Toluenesulfonyl chloride → HCID 86691871, compound

HRID 517712Notes

Reaction equation

HRID 517712 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C(N(CC)CC)C.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl.CN(C)C1C=CN=CC=1>[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH:5]([CH2:8][O:9][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=2)(=[O:32])=[O:31])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 57355258tert-Butyl 2,5-bis(hydroxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 86691871HCID 86691871, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl 2,5-bis(hydroxymethyl)-1-pyrrolidinecarboxylate (commercially available, for example from J&W Pharmlab, 7.57 g, 32.7 mmol) in dichloromethane (200 mL) was added triethylamine (4.79 mL, 34.4 mmol), 4-dimethylaminopyridine (0.20 g, 1.64 mmol) and p-toluenesulfonyl chloride (6.55 g, 34.4 mmol). The reaction was stirred at room temperature for 18 hours. The reaction was diluted with DCM (200 mL) and the solution washed with water (200 mL). The organic layer was collected via a hydrophobic frit and the solvent removed under vacuum. The residue was purified by silica chromatography (Biotage SP4, eluting 30% EtOAc in iso-hexane (3 column volumes), a gradient from 30-50% (over 6 column volumes) then 50% EtOAc (3 column volumes)) to yield the title compound as a colourless gum (2.28 g).

Workup

  1. washthe solution washed with water (200 mL)
  2. customThe organic layer was collected via a hydrophobic frit
  3. customthe solvent removed under vacuum
  4. customThe residue was purified by silica chromatography (Biotage SP4
  5. washeluting 30% EtOAc in iso-hexane (3 column volumes)

Sources & evidence

ORD record
ord-dbd1c8575a3f4d579efa297002ffcf24
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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