Triethylamine → (R*)-3-[1-((R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)piperidin-3-yl]benzoic acid methyl ester

HRID 2365961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365961
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11](Cl)=[O:12].[CH3:14][O:15][C:16](=[O:29])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]2)[CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:14][O:15][C:16](=[O:29])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C@H:23]2[CH2:28][CH2:27][CH2:26][N:25]([C:11]([C@@H:2]3[O:1][C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[O:4][CH2:3]3)=[O:12])[CH2:24]2)[CH:18]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 7022160(R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl chlorideHCID 12937924Methyl 3-(piperidin-3-yl)benzoate

Produkt 1

HCID 68489387(R*)-3-[1-((R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)piperidin-3-yl]benzoic acid methyl esterAusbeute 21,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl chloride (240 mg, 1.21 mmol) in DCM (5 ml) was added to an ice-cold mixture of 3-(piperidin-3-yl)benzoic acid methyl ester (267 mg, 1.21 mmol), triethylamine (59 mg, 0.58 mmol) and DCM (10 ml). After stirring for 2 h at RT, the mixture was washed with 1 M HCl (10 ml) and 1 M Na2CO3. The organic phase was dried over Na2SO4 and evaporated to dryness and the residue was purified by flash chromatography using heptane/EtOAc as eluent. The first eluting diastereomer was collected to afford 98 mg of the title compound.

Aufarbeitung

  1. washthe mixture was washed with 1 M HCl (10 ml) and 1 M Na2CO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated to dryness
  4. customthe residue was purified by flash chromatography
  5. customThe first eluting diastereomer was collected

Quellen und Nachweise

ORD-Eintrag
ord-f48f0c61e6e749d4b74b1a772609aefa
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697723B2

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