p-Toluenesulfonic acid → HCID 57421405, compound

HRID 641935Notes

Reaction equation

HRID 641935 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 560953Benzyl 3-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 57421405HCID 57421405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 250 mL 3-necked round bottom flask was placed a solution of benzyl 3-hydroxypyrrolidine-1-carboxylate (10 g, 45.23 mmol) in CH2Cl2 (100 mL). To this was added 3,4-dihydro-2H-pyran (19 g, 226.19 mmol). To the mixture was added p-toluenesulfonic acid (389 mg, 2.26 mmol) and the resulting solution was allowed to react, with stirring, for 10 minutes while the temperature was maintained at 0° C. The resulting solution was allowed to react, with stirring, for an additional 1 hour at room temperature. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:2). The reaction mixture was then quenched by the adding 100 mL of NaHCO3. The resulting mixture was washed with 100 mL of NaHCO3 and 100 mL of brine. The mixture was dried over MgSO4 and concentrated under vacuum using a rotary evaporator. This resulted in 15 g (98%) of benzyl 3-(tetrahydro-2H-pyran-2-yloxy)pyrrolidine-1-carboxylate as yellow oil.

Workup

  1. customInto a 250 mL 3-necked round bottom flask was placed
  2. customto react
  3. customto react
  4. stirringwith stirring, for an additional 1 hour at room temperature
  5. customThe reaction mixture was then quenched by the adding 100 mL of NaHCO3
  6. washThe resulting mixture was washed with 100 mL of NaHCO3 and 100 mL of brine
  7. dry with materialThe mixture was dried over MgSO4
  8. concentrationconcentrated under vacuum
  9. customa rotary evaporator
  10. customThis resulted in 15 g (98%) of benzyl 3-(tetrahydro-2H-pyran-2-yloxy)pyrrolidine-1-carboxylate as yellow oil

Sources & evidence

ORD record
ord-7274462d501349659e75536a78a92974
Source dataset
uspto-grants-2010_04
Patent number
US07696229B2

Reaction notes

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