Sodium hydride → HCID 86586689, compound

HRID 2088156Notes

Reaction equation

HRID 2088156 reaction equation
[H-].[Na+].[C:3]([CH:5]1[C:11]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]([CH2:13][CH:14]=[CH2:15])[CH:7]([CH2:8][CH2:9][CH:10]2[OH:22])[CH2:6]1)#[N:4].[F:23][C:24]([F:38])([F:37])[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:28]Br.C1OCCOCCOCCOCCOCCOC1>C1COCC1>[F:23][C:24]([F:37])([F:38])[C:25]1[CH:26]=[C:27]([CH2:28][O:22][C@@H:10]2[CH2:9][CH2:8][C@@H:7]3[N:12]([CH2:13][CH:14]=[CH2:15])[C@@:11]2([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:5]([C:3]#[N:4])[CH2:6]3)[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 69890894HCID 69890894, compound

Product 1

HCID 86586689HCID 86586689, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil, 28 mg, 0.7 mmol) was added to a stirred mixture of 1R*,2R*,5S*,7S*)-7-cyano-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octan-2-ol (Description 25; 50 mg, 0.18 mmol), 3,5-bis(trifluoromethyl)benzyl bromide (0.6 ml, 3.27 mmol) and 18-crown-6 (38 mg, 0.14 mmol) in THF (4 ml) at room temperature. The reaction mixture was stirred for 20 hours, quenched with brine and extracted into dichloromethane. The combined organic extracts were washed with water, dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate) to give the title compound (68 mg, 74%).

Workup

  1. customquenched with brine
  2. extractionextracted into dichloromethane
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate)

Sources & evidence

ORD record
ord-decb7b781d554eecb68a00c1388b7fd6
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

Loading…