(R)-3-Pyrrolidinol → HCID 66917412, compound

HRID 2355226Notes

Reaction equation

HRID 2355226 reaction equation
F[C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21]OS(C)(=O)=O)[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[OH:27][C@@H:28]1[CH2:32][CH2:31][NH:30][CH2:29]1>CN1C(=O)CCC1>[C:4]1([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][CH:17]([CH2:21][N:30]4[CH2:31][CH2:32][C@@H:28]([OH:27])[CH2:29]4)[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 58869139HCID 58869139, compound

Product 1

HCID 66917412HCID 66917412, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

Methanesulfonic acid (R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl ester (0.052 g, 0.13 mmol), (R)-3-hydroxypyrrolidine (0.035 g) and NMP (0.5 mL were sealed in a tube and heated to 110° C. for 18 hours. The reaction mixture was cooled and partitioned between water and diethyl ether. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to give 40.6 mg of (R)-1-(7-benzenesulfonyl-chroman-2-ylmethyl)-pyrrolidin-3-ol, MS (M+H)=374.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between water and diethyl ether
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b35391d2f19b4fd0853bba5aa4540a49
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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