Triphenylphosphine → dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]phthalate

HRID 350352

Reaktionsgleichung

Reaktionsgleichung von HRID 350352
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].[C:16]([N:23]1[CH2:29][CH2:28][CH2:27][C@H:24]1[CH2:25]O)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:19]([O:18][C:16]([N:23]1[CH2:29][CH2:28][CH2:27][C@H:24]1[CH2:25][O:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:17])([CH3:22])([CH3:20])[CH3:21]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 89726Dimethyl 4-hydroxyphthalateHCID 643448(S)-(-)-N-Boc-prolinolHCID 5363146Diisopropyl azodicarboxylate

Produkt 1

HCID 86587781dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]phthalateAusbeute 102,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of dimethyl 4-hydroxyphthalate (3.00 g, 14.27 mmol), N-Boc-prolinol (2.87 g, 14.26 mmol), Ph3P (4.49 g, 17.12 mmol) in THF (50 mL) was added DIAD (3.40 mL, 17.27 mmol) at 0° C. Then the resulting mixture was heated under reflux overnight. The resulting mixture was evaporated and the residue was purified by column chromatography on silica-gel with n-hexane-EtOAc (3:1, v/v) as eluent to give 5.75 g (q.y.) dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinyl methoxy]phthalate as an oil. 1H-NMR (CDCl3) δ 1.47 (s, 9 H), 1.86–2.05 (m, 4 H), 3.36–3.40 (m, 2 H), 3.87 (m, 3 H), 3.91 (s, 3 H), 3.96–4.19 (m, 3 H), 7.03–7.24 (m, 2 H), 7.80 (m, 1H).

Aufarbeitung

  1. temperatureThen the resulting mixture was heated
  2. temperatureunder reflux overnight
  3. customThe resulting mixture was evaporated
  4. customthe residue was purified by column chromatography on silica-gel with n-hexane-EtOAc (3:1

Quellen und Nachweise

ORD-Eintrag
ord-380a6cafc6304821b828eb1d927d7463
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179819B2

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