Sodium Hydroxide → HCID 68643973, compound

HRID 2388667Notes

Reaction equation

HRID 2388667 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[CH2:18][OH:19])(=[O:12])=[O:11])=[C:5]([CH3:20])[CH:4]=1.[OH-].[Na+].Br[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:20])[C:6]([S:10]([N:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[CH2:18][O:19][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])(=[O:11])=[O:12])=[C:7]([CH3:9])[CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 59401705HCID 59401705, compound

Product 1

HCID 68643973HCID 68643973, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-(1-(4-methoxy-2,6-dimethylphenylsulfonyl)pyrrolidin-2-yl)methanol (2.7 g, 9.0303 mmol) in dichloromethane (45 ml) was added 35% aq NaOH solution (45 ml) followed by addition of tetra-n-butylammonium chloride (290 mg, 0.09308 mmol). The reaction mixture was stirred for 15 min at room temperature. Then it was cooled to 0° C. and tert-butyl 2-bromoacetate (1.7 ml, 10.83 mmol) was added and the mixture stirred for 2 h at room temperature. After completion of the reaction the organic layer was separated and washed with water and brine. The organic layer was dried over sodium sulfate and purified by column chromatography. Yield: 81%.

Workup

  1. temperatureThen it was cooled to 0° C.
  2. stirringthe mixture stirred for 2 h at room temperature
  3. customAfter completion of the reaction the organic layer
  4. customwas separated
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-a541ef8db8ed4f02b050a2719c84c53a
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

Loading…