Triethylamine → HCID 60052341, compound

HRID 423401Notes

Reaction equation

HRID 423401 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]2)=[N:6][CH:7]=1.CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][C@@H:10]([O:13][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57365913(3R)-1-(5-Bromopyridin-2-yl)pyrrolidin-3-ol

Product 1

HCID 60052341HCID 60052341, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve (R)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-ol (6.8 g, 27.64 mmol), (prepare according to Stenkamp, D. et al WO 2005103032) in CH2Cl2 (50 mL), and cool to 0° C. Treat the mixture with Et3N (5.0 mL, 35.93 mmol), followed by MsCl (2.4 mL, 30.4 mmol). Stir the mixture at 0° C. for 30 min and then at RT for 1 h. Dilute with CH2Cl2 (100 mL), and wash with H2O (100 mL), and brine (100 mL). Dry with Na2SO4, filter, and concentrate. Purify the crude material by chromatography, eluting with 50-70% EtOAc/hexane, to give 8.86 g (97%) of the title compound. MS/ES m/z (79Br) 321.0 [M+H]+.

Workup

  1. dissolutionDissolve
  2. waitat RT for 1 h
  3. washwash with H2O (100 mL), and brine (100 mL)
  4. dry with materialDry with Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by chromatography
  8. washeluting with 50-70% EtOAc/hexane

Sources & evidence

ORD record
ord-c37bc0c2725e4518ae7cc61e0af356d5
Source dataset
uspto-grants-2012_01
Patent number
US08101764B2

Reaction notes

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