Water → HCID 178463899, compound

HRID 634769Notes

Reaction equation

HRID 634769 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C@H:21]2[CH2:26][CH2:25][C@H:24]([N:27]([CH2:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28](=O)[CH3:29])[CH2:23][CH2:22]2)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C@H:21]2[CH2:22][CH2:23][C@H:24]([N:27]([CH2:28][CH3:29])[CH2:31][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:25][CH2:26]2)=[CH:17][CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178474715HCID 178474715, compound

Product 1

HCID 178463899HCID 178463899, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of LiAlH4 (74 mg, 1.95 mmol) and THF (10 ml) at 0° under Argon, a solution of trans-N-[4-(4-benzyloxy-phenyl)-cyclohexyl]-N-(3-phenyl-propyl)-acetamide (0.43 g, 0.97 mmol) in THF (10 ml) was added. The suspension was stirred for 2 h at RT and for 1 h at reflux. After cooling to 0°, H2O (0.4 ml) was carefully added, followed by 15% NaOH (0.4 ml) and H2O (0.4 ml). The precipitate was removed by filtration and the filtrate dried over Na2SO4, and evaporated. The residue was purified by chromatography over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH 95:5 to give trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-ethyl-(3-phenyl-propyl)-amine (0.11 g, 26%) as a colorless oil. MS: m/e=328.5 (M+H+).

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling to 0°
  3. customThe precipitate was removed by filtration
  4. dry with materialthe filtrate dried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by chromatography over SiO2 (Merck 230-400 mesh)
  7. washeluting with CH2Cl2—MeOH 95:5

Sources & evidence

ORD record
ord-d8658bc8ed0a4fc79efd861e0ed0e502
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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