7-[3-(4-carboxy-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester → 4-[3-(4,4-Dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-ynyl]-benzoic acid

HRID 899304Notes

Reaction equation

HRID 899304 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:19]#[C:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=3)[CH:16]=2)[C:11]([CH3:36])([CH3:35])[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[CH3:35][C:11]1([CH3:36])[C:12]2[C:17](=[CH:16][C:15]([CH:18]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:19]#[C:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([OH:29])=[O:28])=[CH:25][CH:26]=3)=[CH:14][CH:13]=2)[NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 692139537-[3-(4-carboxy-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 102716564-[3-(4,4-Dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-ynyl]-benzoic acidYield 73.3%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 7-[3-(4-carboxy-phenyl)-1-pentyl-prop-2-ynyl]-4,4-dimethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (0.035 g, 0.07 mmole) in 2 mL of a 1:1 TFA/dichloromethane mixture was stirred for 30 minutes and concentrated. The residue was dissolved in 5 mL of dichloromethane and washed with 5 ml of saturated sodium bicarbonate, 5 mL of water and 5 mL of brine, the organic layer was dried over MgSO4, filtered and concentrated in vacuo to give 0.02 g of 4-[3-(4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-oct-1-ynyl]-benzoic acid as brownish oil. MS (ESI): (M−): 388.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 5 mL of dichloromethane
  3. washwashed with 5 ml of saturated sodium bicarbonate, 5 mL of water and 5 mL of brine
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fedb58904e54da2b0fea240dc89f1ab
Source dataset
uspto-grants-2008_04
Patent number
US07354931B2

Reaction notes

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