4-Toluenesulfonyl chloride → 3-Tosyl-Cbz-(R)-Pyrrolidine

HRID 2087087Notes

Reaction equation

HRID 2087087 reaction equation
O[C@@H: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.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[S:23]([C@@H: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)([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinol

Product 1

HCID 671827093-Tosyl-Cbz-(R)-PyrrolidineYield 94.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Hydroxy-Cbz-(R)-pyrrolidine (13.7 g, 0.06 mol) was dissolved in CH2Cl2 (250 mL) and cooled to 0° C. p-Toluenesulfonyl chloride (14.16 g, 0.07 mol), and triethylamine (20.7 mL, 0.15 mol) were added and the resulting solution was stirred for 4 h at 0° C. The solution was washed with 1 M HCl, saturated NaHCO3, and brine. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate/hexanes (3/1, v/v) to afford 20.4 g (88% yield) of the desired product as an oil.

Workup

  1. additionwere added
  2. washThe solution was washed with 1 M HCl, saturated NaHCO3, and brine
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography
  6. washeluting with ethyl acetate/hexanes (3/1

Sources & evidence

ORD record
ord-47499b2727b84624a09dd8aa63f61f0a
Source dataset
uspto-grants-2004_04
Patent number
US06727368B1

Reaction notes

Loading…