Reaktion #170047

ord-9606b7a3272f4cd9ae3ecceadf9ef301

Reaktionsgleichung

CC(C)(C)OC(=O)NC1CCc2ccc(CN)cc2C1Cc1ccccc1
tert-Butyl 7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate
CCN(CC)CC
triethylamine
CCCS(=O)(=O)Cl
1-Propanesulfonyl chloride
CCCS(=O)(=O)NCc1ccc2c(c1)C(Cc1ccccc1)C(NC(=O)OC(C)(C)C)CC2
product
Ausbeute 81.2%
CCCS(=O)(=O)NCc1ccc2c(c1)C(Cc1ccccc1)C(NC(=O)OC(C)(C)C)CC2
tert-Butyl 1-benzyl-7-(propylsulfonamidomethyl)-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate
Ausbeute 81.2%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISSOLUTIONThe solid immediately dissolved
  2. 2
    Waschenwashed with brine (1×50 mL)
  3. 3
    SonstigeThe organic phase was collected
  4. 4
    Sonstigedried on MgSO4
  5. 5
    Sonstigethe volatiles were evaporated under reduced pressure

Vorschrift

tert-Butyl 7-(aminomethyl)-1-benzyl-1,2,3,4-tetrahydronaphthalen-2-ylcarbamate (0.600 g, 1.637 mmol) was suspended in dichloromethane (5 mL) and triethylamine (0.228 mL, 1.637 mmol) and cooled to 0° C. 1-Propanesulfonyl chloride (0.184 mL, 1.64 mmol) was added. The solid immediately dissolved. The mixture was stirred 35 minutes, and then it was diluted with dichloromethane and washed with brine (1×50 mL). The organic phase was collected, dried on MgSO4 and the volatiles were evaporated under reduced pressure, yielding the product as a pale yellow solid (628.3 mg, 1.33 mmol, 81%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846741B2uspto-grants-2014_09