HCID 69311864, compound → HCID 69311925, compound

HRID 1947041Notes

Reaction equation

HRID 1947041 reaction equation
[C:1]([Si:5]([CH3:36])([CH3:35])[O:6][CH2:7][CH2:8][N:9]([CH:14]1[CH2:19][CH2:18][CH:17]([N:20](CC2C=CC=CC=2)CC2C=CC=CC=2)[CH2:16][CH2:15]1)[S:10]([CH3:13])(=[O:12])=[O:11])([CH3:4])([CH3:3])[CH3:2]>CCO.CO.[OH-].[OH-].[Pd+2]>[C:1]([Si:5]([CH3:36])([CH3:35])[O:6][CH2:7][CH2:8][N:9]([CH:14]1[CH2:15][CH2:16][CH:17]([NH2:20])[CH2:18][CH2:19]1)[S:10]([CH3:13])(=[O:12])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 69311864HCID 69311864, compound

Product 1

HCID 69311925HCID 69311925, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

N-[2-(t-Butyl-dimethyl-silanyloxy)-ethyl]-N-(4-dibenzylamino-cyclohexyl)-methanesulfonamide (3.282 g, 6.18 mmol) and Pd(OH)2 (0.40 g) were combined in EtOH/MeOH under Ar, and treated with H2 (45 psi) at RT for 1 day. The reaction mixture was then filtered, the solid washed with EtOH, the filtrates combined, and solvent removed in vacuo to yield N-[2-(t-butyl-dimethyl-silanyloxy)-ethyl]-N-(4-amino-cyclohexyl)-methanesulfonamide (2.123 g).

Workup

  1. additiontreated with H2 (45 psi) at RT for 1 day
  2. filtrationThe reaction mixture was then filtered
  3. washthe solid washed with EtOH
  4. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-ee2a598afe14461981414f678f97282a
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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