6-(5-Hydroxy-pent-1-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester → 6-(5-Hydroxy-pentyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 49490Notes

Reaction equation

HRID 49490 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]#[C:19][CH2:20][CH2:21][CH2:22][OH:23])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 695148486-(5-Hydroxy-pent-1-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 695152756-(5-Hydroxy-pentyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl esterYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

850 mg (2.7 mmol) 6-(5-Hydroxy-pent-1-ynyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester in 30 ml ethanol were hydrogenated in the presence of 10% Pd/C over night. Purification by column chromatography yielded 450 mg (68%) 6-(5-Hydroxy-pentyl)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as yellow oil, MS: 319 (M).

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-f7e564e50c364d008494d3586b876083
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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