Triethylamine → HCID 53950456, compound

HRID 2210004Notes

Reaction equation

HRID 2210004 reaction equation
[CH3:1][N:2]1[CH2:6][C@H:5]([CH2:7][OH:8])[C@H:4]([CH2:9][OH:10])[CH2:3]1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[CH3:1][N:2]1[CH2:6][C@H:5]([CH2:7][O:8][S:19]([CH3:18])(=[O:21])=[O:20])[C@H:4]([CH2:9][O:10][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54288325HCID 54288325, compound

Product 1

HCID 53950456HCID 53950456, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To an ice cooled solution of 6.2 gm (43 mMol) 1-methyl-cis-3,4-di(hydroxymethyl) pyrrolidine and 14.5 gm(143 mMol ) triethylamine in 200 mL dichloromethane was added a solution of 14.7 gm (129 mMol) methanesulfonyl chloride in 20 mL dichloromethane. Once this addition was complete the reaction mixture was stirred for 15 minutes at 0° C. and then for 1.5 hours at ambient. The reaction mixture was then quenched with dilute aqueous sodium hydroxide solution and then was extracted with dichloromethane. The organic phase was dried over sodium sulfate and then concentrated in vacuo to give 9.6 gm of the desired compound as an orange oil.

Workup

  1. additionOnce this addition
  2. waitfor 1.5 hours at ambient
  3. customThe reaction mixture was then quenched with dilute aqueous sodium hydroxide solution
  4. extractionwas extracted with dichloromethane
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3adb156b6b1c4482a4e7067d95c5624b
Source dataset
uspto-grants-1995_10
Patent number
US05457121

Reaction notes

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