Dimethyl Sulfide → 7-(4-(Trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane

HRID 2110164Notes

Reaction equation

HRID 2110164 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:17](=O)[CH:16]3[NH:19][CH:12]([CH2:13][S:14][CH2:15]3)[C:11]2=O)=[CH:6][CH:5]=1.S(C)C.FC(F)(F)C1C=CC(C2CCNCC=2)=CC=1.[OH-].[Na+]>C1COCC1>[F:22][C:2]([F:1])([F:21])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:17][CH:16]3[NH:19][CH:12]([CH2:13][S:14][CH2:15]3)[CH2:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 14798Sodium HydroxideHCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-HCID 689586847-(4-(Trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane-6,8-dione

Product 1

HCID 689658697-(4-(Trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-(4-(trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane-6,8-dione (115 mg, 0.35 mmol) and THF (5 mL) was heated at 70° C. under N2. A solution of BH3.SMe2 (2M in THF, 0.7 mL, 1.4 mmol) was added dropwise. After 2.5 h, 6N HCl (1.0 mL) was added dropwise (Caution: H2 evolution). After an additional 30 min, the reaction was allowed to cool to rt, poured into 1N NaOH (8 mL), and extracted with dichloromethane (40 mL×2). The combined organic extracts were dried, filtered and concentrated to give 7-(4-(trifluoromethoxy)phenyl)-3-thia-7,9-diazabicyclo[3.3.1]nonane: MS (ESI): 305.5 (M+H).

Workup

  1. waitAfter an additional 30 min
  2. extractionextracted with dichloromethane (40 mL×2)
  3. customThe combined organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a768dab51e014fafb6ad9f7427cbcc3c
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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