Sodium hydride → HCID 86586687, compound

HRID 2088154Notes

Reaction equation

HRID 2088154 reaction equation
[H-].[Na+].[C:3]([CH:5]1[CH2:11][C:10]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]([CH2:13][CH:14]=[CH2:15])[CH:6]1[CH2:7][CH2:8][CH:9]2[OH:22])#[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:9]2[CH2:8][CH2:7][C@@H:6]3[N:12]([CH2:13][CH:14]=[CH2:15])[C@@:10]2([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][C@H:5]3[C:3]#[N:4])[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 69890662HCID 69890662, compound

Product 1

HCID 86586687HCID 86586687, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil, 100 mg, 2.5 mmol) was added to a stirred mixture of 1R*,2R*,5S*,6R*)-6-cyano-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octan-2-ol (Description 24; 400 mg, 1.49 mmol), 3,5-bis(trifluoromethyl)benzyl bromide (1 ml, 5.45 mmol) and 18-crown-6 (87 mg, 0.33 mmol) in THF (5 ml) at room temperature. The reaction mixture was stirred for 22 hours, quenched with water 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 (530 mg, 72%).

Workup

  1. customquenched with water
  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-1d6165629608419f98e402a813a572c1
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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