Potassium Carbonate → HCID 86682909, compound

HRID 2368939Notes

Reaction equation

HRID 2368939 reaction equation
CS(O[C@H:6]([CH3:28])[CH2:7][O:8][C:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)=O.Cl.[F:30][C@@H:31]1[CH2:35][CH2:34][NH:33][CH2:32]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[F:30][C@@H:31]1[CH2:35][CH2:34][N:33]([C@@H:6]([CH3:28])[CH2:7][O:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:32]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2759162(3R)-3-fluoropyrrolidine hydrochlorideHCID 13777646HCID 13777646, compound

Product 1

HCID 86682909HCID 86682909, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-1-(trityloxy)propan-2-yl methanesulfonate (1.25 g, 3.15 mmol), (R)-3-fluoropyrrolidine hydrochloride (480 mg, 3.52 mmol), and K2CO3 (1.31 g, 9.48 mmol) in acetonitrile (40 mL) was heated at reflux for 4 days. The reaction was cooled to room temperature, concentrated under reduced pressure, and diluted with DCM (100 mL). The solution was washed (50 mL sat'd NaHCO3), dried (Naz SO4), and concentrated under reduced pressure. The crude material was purified on a silica gel column to yield (R)-3-fluoro-1-((S)-1-(trityloxy)propan-2-yl)pyrrolidine (725 mg) as a pale brown oil. 1H NMR (CDCl3): δ 7.60-7.20 (m, 15H), 5.40-4.95 (m, 1H), 3.30 (m, 1H), 3.05-2.50 (m, 5H), 2.29 (m, 1H), 2.06-1.70 (m, 2H), 1.07 (d, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 days
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with DCM (100 mL)
  5. washThe solution was washed (50 mL sat'd NaHCO3)
  6. customdried (Naz SO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified on a silica gel column

Sources & evidence

ORD record
ord-da35c2e9142047dab20c91d790ac0e88
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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