Acetic Acid → 1,1-Dimethylethyl 2-[[[[4-(methoxycarbonyl)phenyl]methyl]amino]methyl]-1-pyrrolidinecarboxylate

HRID 630326

Reaktionsgleichung

Reaktionsgleichung von HRID 630326
[NH2:1][CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH:15]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH3:24][O:23][C:21]([C:20]1[CH:25]=[CH:26][C:17]([CH2:15][NH:1][CH2:2][CH:3]2[CH2:7][CH2:6][CH2:5][N:4]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:18][CH:19]=1)=[O:22]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 15294Methyl 4-FormylbenzoateHCID 516892Sodium BicarbonateHCID 2756484(+-)-2-(Aminomethyl)-1-N-Boc-pyrrolidineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 684903891,1-Dimethylethyl 2-[[[[4-(methoxycarbonyl)phenyl]methyl]amino]methyl]-1-pyrrolidinecarboxylateAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

A solution of 1,1-dimethylethyl 2-(aminomethyl)-1-pyrrolidinecarboxylate (1000 mg, 5 mmol) and methyl 4-formylbenzoate (820 mg, 5 mmol) in dichloroethane was stirred as acetic acid (450 mg, 7.5 mmol) and sodium triacetoxyborohydride (1271 mg, 6 mmol) were added sequentially at ambient temperature. After stirring at ambient temperature for 17 hours, treated with a saturated aqueous solution of sodium bicarbonate and extracted with EtOAc. The combined organic extracts were dried and concentrated. Purification by flash chromatography afforded 1,1-dimethylethyl 2-[[[[4-(methoxycarbonyl)phenyl]methyl]amino]methyl]-1-pyrrolidinecarboxylate (800 mg), 1H NMR (CDCl3) 7.98 (d, 2H), 3.37 (d, 2H), 3.91 (s, 3H), 3.82 (s, 2H), 3.36 (m, 2H), 2.72 (m, 1H), 1.82 (m, 3H), 1.44 (m, 2H) ppm.

Aufarbeitung

  1. additionwere added sequentially at ambient temperature
  2. extractionextracted with EtOAc
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c9e299d2e7174c1685611cfd82b75f95
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315509B2

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