Chloroacetyl chloride → HCID 57440632, compound

HRID 1882531Notes

Reaction equation

HRID 1882531 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-dfb8d8c7abfb4b1487c4aafbe0d97b5e
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

Loading…