Triethylamine → (S)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methyl methanesulfonate

HRID 517951Notes

Reaction equation

HRID 517951 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:11][CH2:10][C@H:9]([CH2:12][OH:13])[CH2:8]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:13][CH2:12][C@H:9]1[CH2:10][CH2:11][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:8]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67294196(S)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methanol

Product 1

HCID 86673348(S)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-(1-(Pyridin-2-yl)pyrrolidin-3-yl)methanol (1.683 mmol, 0.3 g) and triethylamine (5.05 mmol, 0.702 ml, 0.511 g) were stirred in DCM (10 ml) at 0° C. Methanesulfonyl chloride (2.52 mmol, 0.195 ml, 0.289 g) was added and the reaction allowed to warm to room temperature over 1 hour. The reaction mixture was washed with water, dried over Na2SO4 and concentrated at reduced pressure to afford (S)-(1-(pyridin-2-yl)pyrrolidin-3-yl)methyl methanesulfonate. (0.38 g)

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-465e58b1b9824d4d84fffc0c49226cd9
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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