Triethylamine → (S)-1-((Benzyloxy)carbonyl)pyrrolidin-3-yl methanesulfonate

HRID 1601720Notes

Reaction equation

HRID 1601720 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.C(N(CC)CC)C.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>C(OCC)(=O)C.O>[CH3:27][S:24]([O:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1)(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinol

Product 1

HCID 14555474(S)-1-((Benzyloxy)carbonyl)pyrrolidin-3-yl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7.3 g of benzyl (R)-3-hydroxy-pyrrolidine-1-carboxylate and 5.56 ml of triethylamine in 80 ml of ethyl acetate was cooled to 0-5° C. under argon and treated within 30 minutes with a solution of 2.97 ml of mesyl chloride in 20 ml of ethyl acetate. After stirring at room temperature for 2 hours and leaving to stand for 16 hours the suspension was diluted with 40 ml of water, stirred for 10 minutes and the organic phase was separated. The organic phase was extracted in succession with 20 ml of 1N HCl, 20 ml of saturated NaHCO3 solution and 10 ml of saturated NaCl solution. The organic phase was dried over Na2SO4, filtered and the filtrate was concentrated to give 10.18 g of product as a beige oil.

Workup

  1. customleaving
  2. waitto stand for 16 hours
  3. stirringstirred for 10 minutes
  4. customthe organic phase was separated
  5. extractionThe organic phase was extracted in succession with 20 ml of 1N HCl, 20 ml of saturated NaHCO3 solution and 10 ml of saturated NaCl solution
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f3b9134686064869be273c2e6f989c4b
Source dataset
uspto-grants-1999_11
Patent number
US05977381

Reaction notes

Loading…