Chloroacetyl chloride → HCID 57440632, compound

HRID 2382378Notes

Reaction equation

HRID 2382378 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:15][C:16](Cl)=[O:17].[NH:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1>C1COCC1>[C:1]([O:5][C:6](=[O:13])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:16](=[O:17])[CH2:15][N:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 79341Piperidin-4-olHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 57440632HCID 57440632, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (1.5 g, 8.1 mmol) in THF (150 ml) is added TEA (2.3 ml, 16.1 mmol) followed by dropwise addition of chloroacetyl chloride (0.67 ml, 8.5 mmol). The reaction mixture is allowed to stir at room temperature for 2 hours and then treated TEA (2.3 ml, 16.1 mmol) followed by 4-piperidinol (4.07 g, 40.3 mmol). After stirring at 50° C. for 18 hours, the solvent is removed in vacuo and purification of the crude residue by reverse phase column chromatography (Isolute™ C18, 0-100% MeOH in water—0.1% TFA) to yield the title product. [MH+ 328.19].

Workup

  1. stirringAfter stirring at 50° C. for 18 hours
  2. customthe solvent is removed in vacuo and purification of the crude residue by reverse phase column chromatography (Isolute™ C18, 0-100% MeOH in water—0.1% TFA)

Sources & evidence

ORD record
ord-3cc6819df84e4f88a418a16beef71cfc
Source dataset
uspto-grants-2012_09
Patent number
US08258141B2

Reaction notes

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