Ethanol → 4,5,6,7-Tetrahydro-1,3a,3b,8-tetraaza-cyclopenta[a]indene-2-carbaldehyde
Reaction equation
[H-].C([O:4][C:5]([C:7]1[N:8]=[C:9]2[N:17]=[C:16]3[N:11]([CH2:12][CH2:13][CH2:14][CH2:15]3)[N:10]2[CH:18]=1)=O)C.C(O)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C1COCC1.C(OCC)(=O)C>[N:8]1[C:7]([CH:5]=[O:4])=[CH:18][N:10]2[N:11]3[C:16]([CH2:15][CH2:14][CH2:13][CH2:12]3)=[N:17][C:9]=12Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -78 °C
Procedure
1.01 M Diisobutylalminium hydride in toluene (1.06 mL) was added dropwise to the solution of 4,5,6,7-tetrahydro-1,3a,3b,8-tetraaza-cyclopenta[a]indene-2-carboxylic acid ethyl ester (100 mg) in dry THF (5 mL) at −78° C. under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes at −78° C. and treated with ethanol (ca. 1 mL). The mixture was warmed to 0° C. and stirred for 1 h at 0° C. The reaction solution was diluted with ethyl acetate (20 mL), treated with 0.5 mL saturated ammonium chloride solution, and sonicated for ca. 5 minutes (until a precipitate was deposited enough). The mixture was dried (Na2SO4) and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The residue was crystallized from dichloromethane and diethyl ether to give the title compound (47.4 mg, 58%). 1H-NMR (400 MHz, CDCl3) δ 2.16–2.27 (m, 4H), 3.14 (t, 2H, J=6.1 Hz), 4.39 (t, 2H, J=5.7 Hz), 7.53 (s, 1H), 10.01 (s, 1H).
Workup
- temperatureThe mixture was warmed to 0° C.
- stirringstirred for 1 h at 0° C
- customsonicated for ca. 5 minutes (until a precipitate
- dry with materialThe mixture was dried (Na2SO4)
- filtrationfiltered through a pad of Celite
- concentrationThe filtrate was concentrated under reduced pressure
- customThe residue was crystallized from dichloromethane and diethyl ether
Sources & evidence
- ORD record
- ord-a2a03eb6bc084eb3afd3c4d109912c59
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07018997B2
Reaction notes
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