Reaktion #2254220

ord-faa6b2707c3d4c3da08a4159cb6c1cd2

Reaktionsgleichung

O=C(O)C(F)(F)F
TFA
O=CCC1(n2cccn2)CCOC2(CCCC2)C1
2-[9-(1H-pyrazol-1-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehyde
NCc1cccs1
thiophen-2-ylmethanamine
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
c1csc(CNCCC2(n3cccn3)CCOC3(CCCC3)C2)c1
{2-[9-(1H-pyrazol-1-yl)-6-oxaspiro[4.5]decan-9-yl]ethyl}(thiophen-2-ylmethyl)amine
Ausbeute 82.0%

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added
  2. 2
    SonstigeAfter removal of solvent
  3. 3
    Sonstigethe residue was purified by HPLC

Vorschrift

To a mixture of 2-[9-(1H-pyrazol-1-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehyde (15 mg, 0.06 mmol) and thiophen-2-ylmethanamine (19 uL, 0.18 mmol) was stirred at rt for 1 h before NaBH(OAc)3 (25.4 mg, 0.12 mmol) was added. The solution stirred overnight. After removal of solvent, the residue was purified by HPLC to provide {2-[9-(1H-pyrazol-1-yl)-6-oxaspiro[4.5]decan-9-yl]ethyl}(thiophen-2-ylmethyl)amine (17 mg, 61% yield) as a TFA salt. LCMS m/z 346 (M+1) observed.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09044469B2uspto-grants-2015_06