Dimethylformamide → HCID 57669833, compound

HRID 547265Notes

Reaction equation

HRID 547265 reaction equation
[CH:1]([N:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[C:9]([OH:11])=O)([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:15])=O.CN(C=O)C>ClCCl>[CH:1]([N:4]1[CH2:8][CH2:7][CH2:6][C@H:5]1[C:9]([Cl:15])=[O:11])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 45084886L-Proline, 1-(1-methylethyl)- (9CI)

Product 1

HCID 57669833HCID 57669833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-1-isopropylpyrrolidine-2-carboxylic acid (4 g, 23.4 mmol) in dry dichloromethane (40 mL) was added oxalyl chloride (4.4 mL, 46.8 mmol) drop wise under nitrogen at ice bath temperature (0-10° C.). After stirring for 5 min, a drop of dry DMF was added to the reaction mixture and was allowed to stir for 2 h at the same temperature. The volatiles were removed on a rotavapor at reduced pressure and the residue was allowed to stay at high vacuum pump for 1 h to afford (S)-1-isopropylpyrrolidine-2-carbonyl chloride.

Workup

  1. stirringto stir for 2 h at the same temperature
  2. customThe volatiles were removed on a rotavapor at reduced pressure
  3. waitto stay at high vacuum pump for 1 h

Sources & evidence

ORD record
ord-4bcc616c84ab447a85cd866b0027d271
Source dataset
uspto-grants-2011_05
Patent number
US07939513B2

Reaction notes

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