Sodium hydride → HCID 86586781, compound

HRID 2088230Notes

Reaction equation

HRID 2088230 reaction equation
[H-].[Na+].[C:3]1([C:9]23[N:16]([CH2:17][CH:18]=[CH2:19])[CH:13]([CH2:14][CH2:15]2)[CH2:12][CH2:11][CH:10]3[OH:20])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[CH2:26]Br.C1OCCOCCOCCOCCOCCOC1>C1COCC1>[F:21][C:22]([F:35])([F:36])[C:23]1[CH:24]=[C:25]([CH2:26][O:20][C@H:10]2[CH2:11][CH2:12][C@H:13]3[N:16]([CH2:17][CH:18]=[CH2:19])[C@:9]2([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:15][CH2:14]3)[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 22724603HCID 22724603, compound

Product 1

HCID 86586781HCID 86586781, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% in oil, 67 mg, 1.67 mmol) was washed twice with THF and treated with a solution 1S,2S,5S)-1-phenyl-8-(prop-2-enyl)-8-azabicyclo[3.2.1]octan-2-ol (Description 57; 116 mg, 0.47 mmol), 3,5-bis(trifluoromethyl)benzyl bromide (430 mg, 1.4 mmol), 18-crown-6 (33 mg, 1.25 mmol) in THF (2 ml). The reaction mixture was stirred at room temperature overnight, quenched with saturated aqueous NH4Cl and extracted into diethyl ether. The combined organic extracts were washed with water, dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether) to give the title compound.

Workup

  1. additiontreated with a solution
  2. customquenched with saturated aqueous NH4Cl
  3. extractionextracted into diethyl ether
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (iso-hexane:diethyl ether)

Sources & evidence

ORD record
ord-70642af587474db5a2246ec44af3fe09
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

Loading…