p-Bromobenzenesulfonyl chloride → (R)-(1-(4-bromophenylsulfonyl)pyrrolidin-2-yl)methanol

HRID 640609

Reaction equation

HRID 640609 reaction equation
C([O-])(O)=O.[Na+].[NH:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:11][OH:12].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C(Cl)Cl>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:6]2[CH2:10][CH2:9][CH2:8][C@@H:7]2[CH2:11][OH:12])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2724541Prolinol, (R)-

Product 1

HCID 59166148(R)-(1-(4-bromophenylsulfonyl)pyrrolidin-2-yl)methanolYield 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a mixture of sat aq. NaHCO3 (44 g, 0.53 mol), CH2Cl2 (400 mL) and (R)-pyrrolidin-2-yl-methanol (53 g, 0.53 mol) was added 4-bromo-benzenesulfonyl chloride (130 g, 0.50 mol) in CH2Cl2 (100 mL). The reaction was stirred at 20° C. overnight. The organic phase was separated and dried over Na2SO4. Evaporation of the solvent under reduced pressure provided (R)-[1-(4-bromo-benzenesulfonyl)-pyrrolidin-2-yl]-methanol (145 g, crude), which was used in the next step without further purification. 1H NMR (CDCl3, 300 MHz) δ 7.66-7.73 (m, 4H), 3.59-3.71 (m, 3H), 3.43-3.51 (m, 1H), 3.18-3.26 (m, 1H), 1.680-1.88 (m, 3H), 1.45-1.53 (m, 1H).

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0719988129cc4941906d9f3947f6448b
Source dataset
uspto-grants-2010_04
Patent number
US07691902B2

Linked notes

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