Methyl 4-(indol-3-yl)butyrate → 4-(1H-indol-3-yl)butan-1-ol

HRID 378544Notes

Reaction equation

HRID 378544 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][C:13](OC)=[O:14])=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])=[CH:2]1

Participants

4

Reactant 2

HCID 85010Methyl 4-(indol-3-yl)butyrateHCID 21226445Aluminium lithium hydride

Product 1

HCID 111714784-(1H-indol-3-yl)butan-1-olYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution (500 ml) of methyl 4-(3-indolyl)-butyrate (103 g) was added dropwise to a suspension of lithium aluminium hydride (25 g) in tetrahydrofuran (1000 ml) at 40° C. followed by stirring for 1 h at room temperature. Usual work-up gave 4-(3-indolyl)-1-butanol (96 g) as an oil. Arylation with 1-fluoro-4-iodobenzene according to the method described in EXAMPLE 5 yielded 4-[1-[4-fluorophenyl)-3-indolyl]-1-butanol which was converted to the title compound 9a by the method described in EXAMPLE 2 using spiro[1 H-2-benzopyran-4(3H),4'-piperidine]. The maleate salt crystallized from acetone by addition of maleic acid. Yield: 1.5 g, mp: 189-90° C.

Sources & evidence

ORD record
ord-d9651da0d7dd406295ad018893a172ca
Source dataset
uspto-grants-2000_02
Patent number
US06031099

Reaction notes

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