Nonane → 3-(4-Trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane

HRID 2110157Notes

Reaction equation

HRID 2110157 reaction equation
CCCCCCCCC.[F:10][C:11]([F:31])([F:30])[O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:26](=O)[CH:25]3[NH:28][CH:21]([CH2:22][CH2:23][CH2:24]3)[C:20]2=O)=[CH:15][CH:14]=1.FC(F)(F)C1C=CC(C2CCNCC=2)=CC=1.[OH-].[Na+]>C1COCC1>[F:31][C:11]([F:10])([F:30])[O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:26][CH:25]3[NH:28][CH:21]([CH2:22][CH2:23][CH2:24]3)[CH2:20]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 8141NonaneHCID 14798Sodium HydroxideHCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-HCID 670459993-(4-Trifluoromethoxyphenyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione

Product 1

HCID 670460143-(4-Trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo|3.3.1|nonane: A solution of 3-(4-trifluoromethoxyphenyl)-3,9-diaza-bicyclo[3.3.1]nonane-2,4-dione (80 mg, 0.25 mmol) and THF (4 mL) was heated at 70° C. under N2. A solution of BH3—SMe2 (2M in THF, 0.4 mL, 0.8 mmol) was added dropwise. After 40 min, 6N HCl (1.0 mL) was added dropwise (Caution: H2 evolution). After an additional 30 min, the reaction was poured into 1N NaOH (8 mL) and extracted with dichloromethane (30 mL×2). The combined organic extracts were dried, filtered and concentrated to give 3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane: MS (ESI): 287.5 (M+H).

Workup

  1. waitAfter an additional 30 min
  2. extractionextracted with dichloromethane (30 mL×2)
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7bece319a6954c4f91807b971fad55a5
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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