Sodium triacetoxyborohydride → 5-iodo-3-(phenylcarbonyl)-1-(3-{1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione

HRID 12710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12710
[I:1][C:2]1[C:3](=[O:21])[N:4]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])[C:5](=[O:12])[N:6]([CH2:8][CH2:9][CH:10]=O)[CH:7]=1.[F:22][C:23]([F:37])([F:36])[C:24]1[CH:25]=[C:26]([C:30]23[CH2:35][CH:34]2[CH2:33][NH:32][CH2:31]3)[CH:27]=[CH:28][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CC(O)=O.C([O-])(O)=O.[Na+]>[I:1][C:2]1[C:3](=[O:21])[N:4]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])[C:5](=[O:12])[N:6]([CH2:8][CH2:9][CH2:10][N:32]2[CH2:33][CH:34]3[C:30]([C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:22])([F:37])[F:36])[CH:25]=4)([CH2:35]3)[CH2:31]2)[CH:7]=1

Komponenten

7

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 127198501-[3-(Trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexaneHCID 593375793-[5-iodo-2,4-dioxo-3-(phenylcarbonyl)-3,4-dihydro-1(2H)-pyrimidinyl]propanal

Produkt 1

HCID 691348525-iodo-3-(phenylcarbonyl)-1-(3-{1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedioneAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 176Acetic AcidLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-[5-iodo-2,4-dioxo-3-(phenylcarbonyl)-3,4-dihydro-1(2H)-pyrimidinyl]propanal (P38, 350 mg, 0.88 mmol) and (1-[3-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane (racemate, reference procedure for preparation reported in WO2005/080382, 200 mg, 0.88 mmol) in dry DCE (10 ml), AcOH was added and the reaction mixture cooled to 0° C. Sodiumtriacetoxyborohydride (224 mg, 1.055 mmol) was added and the reaction left at 0° C. for 4 hrs. Reaction monitored by LC/MS. The mixture was diluted with a saturated solution of NaHCO3 and extracted with DCM. The solvent was evaporated and the crude purified by silica SPE column (20 g) eluting with acetone/toluene 20:80. After evaporation, 250 mg of the title compound were obtained.

Aufarbeitung

  1. customReaction
  2. extractionextracted with DCM
  3. customThe solvent was evaporated
  4. customthe crude purified by silica SPE column (20 g)
  5. washeluting with acetone/toluene 20:80
  6. customAfter evaporation

Quellen und Nachweise

ORD-Eintrag
ord-3489754114e34fda9f6da7d4c1416108
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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