Triethylamine → HCID 54197046, compound

HRID 617324Notes

Reaction equation

HRID 617324 reaction equation
[CH3:1][N:2]1[CH2:6][C@H:5]([CH2:7][OH:8])[CH2:4][C@H:3]1[CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:17][S:18]([O:8][CH2:7][C@H:5]1[CH2:6][N:2]([CH3:1])[C@H:3]([CH2:9][O:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH2:4]1)(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21309696HCID 21309696, compound

Product 1

HCID 54197046HCID 54197046, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 386 mg (1.84 mmol) sample of 3-(trans-1-methyl-4-hydroxymethyl-2(S)-pyrrolidinylmethoxy)pyridine (from Example 48a above) dissolved in 12 mL of methylene chloride were added 262 μL (3.38 mmol) of methanesulfonyl chloride, 470 μL of triethylamine and a catalytic amount of DMAP, and the reaction mixture was stirred for 5 hours at room temperature. The reaction was quenched with water, the product extracted from the mixture, the solvent removed, and the product purified by column chromatography on silica gel, eluting with 20:1 chloroform:methanol to afford 320 mg of the title compound.

Workup

  1. customThe reaction was quenched with water
  2. extractionthe product extracted from the mixture
  3. customthe solvent removed
  4. customthe product purified by column chromatography on silica gel
  5. washeluting with 20:1 chloroform

Sources & evidence

ORD record
ord-65cc135ebfe74a34855357c015f3ea81
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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