HCID 86620861, compound → 2-(5,6-Dichloro-pyridine-2-carbonyl)-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 661550Notes

Reaction equation

HRID 661550 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[N:19]=1)[OH:17])[CH2:13][CH2:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[N:19]=1)=[O:17])[CH2:13][CH2:14][CH3:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 86620861HCID 86620861, compound

Product 1

HCID 866208622-(5,6-Dichloro-pyridine-2-carbonyl)-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-[(5,6-dichloro-pyridin-2-yl)-hydroxy-methyl]-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.288 g, 0.742 mmol) in DCM (12 mL) at 0° C. under nitrogen was added DMP (0.315 g, 0.742 mmol) in a single portion. The reaction mixture was stirred for one hour, then was quenched with a 1:1 mixture of 10% aqueous Na2S2O3 and saturated aqueous NaHCO3 (50 mL), and extracted with DCM (3×30 mL). The combined oraganic phases were concentrated in vacuo to give 2-(5,6-dichloro-pyridine-2-carbonyl)-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.280 g, 0.725 mmol, 98%) as a yellow solid that was used directly without further purification.

Workup

  1. customwas quenched with a 1:1 mixture of 10% aqueous Na2S2O3 and saturated aqueous NaHCO3 (50 mL)
  2. extractionextracted with DCM (3×30 mL)
  3. concentrationThe combined oraganic phases were concentrated in vacuo

Sources & evidence

ORD record
ord-444f62f1de5949ffafa699429f19f010
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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