Water → 3-Pyrrolidinol, 1-(phenylmethyl)-, 3-methanesulfonate, (3R)-

HRID 2226259Notes

Reaction equation

HRID 2226259 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].O>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 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643472(R)-(+)-1-Benzyl-3-pyrrolidinol

Product 1

HCID 118072543-Pyrrolidinol, 1-(phenylmethyl)-, 3-methanesulfonate, (3R)-Yield 101.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(R)-1-Benzyl-3-hydroxypyrrolidine (3.9 g, 22 mmol) was dissolved in toluene (100 mL) and the solution stirred and cooled to 0°-5° C. Triethylamine (2.66 g, 26.2 mmol) was added followed by methanesulfonyl chloride (3.0 g, 26 mmol). A slurry formed after 30 minutes. The mixture was allowed to warm to room temperature and stirred overnight. Water (100 mL) was added to the reaction mixture and the organic layer separated and washed with water (100 mL) and concentrated under reduced pressure to give (R)-1-benzyl-3-mesyloxypyrrolidine (5.7 g) as a yellow oil: 1HNMR (CDCl3), 60 MHz): δ1.9-2.7 (m, 4H), 2.78 (d, 2H, J=15), 2.90 (s, 3H), 3.65 (s, 2H), 4.9-5.3 (m, 1H), 7.28 (s, 5H).

Workup

  1. temperaturecooled to 0°-5° C
  2. customA slurry formed after 30 minutes
  3. stirringstirred overnight
  4. customthe organic layer separated
  5. washwashed with water (100 mL)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-535046c1d2ff4b3cb9a6ef2b31a66aec
Source dataset
uspto-grants-1994_09
Patent number
US05347017

Reaction notes

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