4-Methoxypiperidine → rac-Cyclopent-1-en-1-yl(4-methoxypiperidin-1-yl)acetic acid

HRID 626449Notes

Reaction equation

HRID 626449 reaction equation
[C:1]1(B(O)O)[CH2:5][CH2:4][CH2:3][CH:2]=1.[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.O.[C:18]([OH:22])(=[O:21])[CH:19]=O.C(N(CC)C(C)C)(C)C>ClCCl>[C:1]1([CH:19]([N:14]2[CH2:15][CH2:16][CH:11]([O:10][CH3:9])[CH2:12][CH2:13]2)[C:18]([OH:22])=[O:21])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

6

Reactant 4

HCID 776664-MethoxypiperidineHCID 81531DiisopropylethylamineHCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 90014907rac-Cyclopent-1-en-1-yl(4-methoxypiperidin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 mg (0.45 mmol) of cyclopent-1-en-1-ylboronic acid, 51 mg (0.45 mmol) of 4-methoxypiperidine 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 2 d 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). This gave 31 mg (29% of theory) of the title compound.

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)

Sources & evidence

ORD record
ord-a2066b1e63eb43a7991e94dc0e867408
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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