Dichloromethane → N-((1R,2R)-2-hydroxy-indan-1-yl)-N-methyl-methanesulphonamide

HRID 1258171Notes

Reaction equation

HRID 1258171 reaction equation
C([Si](C)(C)[O:6][C@@H:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]1[N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])(C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C(Cl)Cl>C1COCC1>[OH:6][C@@H:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]1[N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 58450838N-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-N-methyl-methanesulphonamide

Product 1

HCID 58450840N-((1R,2R)-2-hydroxy-indan-1-yl)-N-methyl-methanesulphonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-indan-1-yl]-N-methyl-methanesulphonamide (0.53 g) is dissolved in 5 mL THF, combined with Bu4NF (5 mL of a 1 N solution in THF) and stirred for 2 h at RT. After the reaction is complete the reaction mixture is freed from the solvent. After the addition of CH2Cl2 it is extracted with HCl (aqu., 1 N). The organic phase is dried on MgSO4. After elimination of the solvent the mixture is purified by normal phase chromatography (CH2Cl2, MeOH). The product-containing fractions are combined and freed from the solvent using the rotary evaporator.

Workup

  1. extractionis extracted with HCl (aqu., 1 N)
  2. customThe organic phase is dried on MgSO4
  3. customAfter elimination of the solvent the mixture is purified by normal phase chromatography (CH2Cl2, MeOH)
  4. customthe rotary evaporator

Sources & evidence

ORD record
ord-475cfb38f78944ef91839239a8c3243c
Source dataset
uspto-grants-2013_06
Patent number
US08466155B2

Reaction notes

Loading…