Triethylamine → (S)-1-Benzyl-3-mesyloxypyrrolidine

HRID 2226257Notes

Reaction equation

HRID 2226257 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 10934081(S)-1-Benzyl-3-mesyloxypyrrolidineYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(S)-1-Benzyl-3-hydroxypyrrolidine (1003.5 g, 5.66 mol) was dissolved in toluene (12 L) and the solution stirred and cooled to 0°-5° C. Triethylamine (680 g, 6.67 mol) was added followed by methanesulfonyl chloride (760 g, 6.63 mol) over a 4 hour period. A slurry formed after 30 minutes. The mixture was allowed to stir an additional 1.5 hours and 7% sodium bicarbonate (12 L) was added to the reaction mixture and the organic layer separated. The aqueous layer was extracted with toluene (4 L and 2 L) and the combined organic layers washed with saturated sodium bicarbonate (3×6 n) , dried over MgSO4 and concentrated under reduced pressure to give (S)-1-benzyl-3-mesyloxy-pyrrolidine as a yellow oil (1.41 kg, 98%): 1HNMR (CDCl3, 200 MHz): δ2.0-2.6 (m, 4H), 2.85 (d, 2H, J=5), 2.97 (δ , 3H), 3.65 (AB, 2H, J=3), 5.20 (m, 1H), 7.3 (m, 5H).

Workup

  1. temperaturecooled to 0°-5° C
  2. customA slurry formed after 30 minutes
  3. stirringto stir an additional 1.5 hours
  4. customthe organic layer separated
  5. extractionThe aqueous layer was extracted with toluene (4 L and 2 L)
  6. washthe combined organic layers washed with saturated sodium bicarbonate (3×6 n)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3db8a65df6f42598e976122ee3ffc4c
Source dataset
uspto-grants-1994_09
Patent number
US05347017

Reaction notes

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