1,2,3,4-Tetrahydroisoquinoline → rac-Cyclopent-1-en-1-yl(3,4-dihydroisoquinolin-2(1H)-yl)acetic acid

HRID 626450Notes

Reaction equation

HRID 626450 reaction equation
[C:1]1(B(O)O)[CH2:5][CH2:4][CH2:3][CH:2]=1.[CH2:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][NH:10]1.O.[C:20]([OH:24])(=[O:23])[CH:21]=O.C(N(CC)C(C)C)(C)C>ClCCl>[C:1]1([CH:21]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9]2)[C:20]([OH:24])=[O:23])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

6

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 81531DiisopropylethylamineHCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 118106377rac-Cyclopent-1-en-1-yl(3,4-dihydroisoquinolin-2(1H)-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg (0.45 mmol) of cyclopent-1-en-1-ylboronic acid, 59.5 mg (0.45 mmol) of 1,2,3,4-tetrahydroisoquinoline and 41 mg (0.45 mmol) of glyoxalic acid monohydrate were initially charged in 2 ml of dichloromethane, and 78 μl (57 mg, 0.45 mmol) of N,N-diisopropylethylamine were added. The mixture was stirred at RT for overnight and then concentrated under reduced pressure. The residue was purified by preparative HPLC (RP18 column; acetonitrile/water gradient with addition of 0.1% TFA, 10:90→95:5; run time 38 min) 101 mg (91% purity, 80% of theory) of the title compound were obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by preparative HPLC (RP18 column; acetonitrile/water gradient with addition of 0.1% TFA, 10:90→95:5; run time 38 min) 101 mg (91% purity, 80% of theory) of the title compound
  3. customwere obtained

Sources & evidence

ORD record
ord-d72239ddebe947ff9ab75560c1afc97b
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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