HCID 18002561, compound → HCID 15411837, compound

HRID 478660Notes

Reaction equation

HRID 478660 reaction equation
[CH:1]1([N:13]2[CH2:30][CH2:29][C:16]3([N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:19](=O)[CH2:18][C:17]3=[O:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.O>[CH:1]1([N:13]2[CH2:30][CH2:29][C:16]3([N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:19][CH2:18][CH2:17]3)[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[CH:1]1([N:13]2[CH2:30][CH2:29][C:16]3([N:20]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:19][CH2:18][CH:17]3[OH:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1

Participants

6

Reactant 2

HCID 18002561HCID 18002561, compoundHCID 21226445Aluminium lithium hydride

Product 2

HCID 15411837HCID 15411837, compoundHCID 18002536HCID 18002536, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-8-(acenaphthen-1-yl)-1-phenyl-1,8-diaza-spiro[4.5]decane-2,4-dione (0.67 g, 1.7 mmol) in THF (35 ml) was added at RT lithium aluminiumhydride (128 mg, 3.4 mmol) and the reaction mixture was boiled under reflux for 7 h. Water (20 drops) was added slowly at RT to the stirred solution and afterwards the reaction mixture was dried (Na2SO4) and filtered. The filtrate was evaporated and the crude product purified by column chromatography on silica gel (ethyl acetate/hexane 9:1) to yield (RS)-8-acenaphthen-1-yl-1-phenyl-1,8-diaza-spiro[4.5]decane (50 mg/see example 20) as a pale yellow oil and 8-(acenaphthen-1-yl)-1-phenyl-1,8-diaza-spiro[4.5]decan-4-ol (127 mg) as a pale brown foam, which while stirring was dissolved in 3N MeOH—HCl (0.5 ml) and treated with diethyl ether (15 ml). After 1 h the solid was filtered off to yield the desired product (128 mg, 55%) as a pale brown solid, m.p. 196° and MS: m/e=385.3 (M+H+).

Workup

  1. temperatureunder reflux for 7 h
  2. dry with materialafterwards the reaction mixture was dried (Na2SO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe crude product purified by column chromatography on silica gel (ethyl acetate/hexane 9:1)

Sources & evidence

ORD record
ord-6449c93e95504dc084b3d90492a9f02f
Source dataset
uspto-grants-2003_11
Patent number
US06642247B2

Reaction notes

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