tert-Butanol → 1-Benzyloxycarbonyl-4-(R)-(1-tert-butoxycarbonylaminocyclopropyl)-3-(R)-methoxypyrrolidine

HRID 1954597Notizen

Reaktionsgleichung

[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][CH3:17])[C@@H:13]([C:18]2(C(O)=O)[CH2:20][CH2:19]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C([N:43]([CH2:46]C)CC)C.[C:48]([OH:52])([CH3:51])([CH3:50])[CH3:49]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][C@H:13]([C:18]2([NH:43][C:46]([O:52][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:31])[CH2:19][CH2:20]2)[C@@H:14]([O:16][CH3:17])[CH2:15]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Edukt 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 542347281-[1-Benzyloxycarbonyl-4-(R)-methoxy-3-(S)-pyrrolidinyl]cyclopropanecarboxylic acid

Produkt 1

HCID 219712631-Benzyloxycarbonyl-4-(R)-(1-tert-butoxycarbonylaminocyclopropyl)-3-(R)-methoxypyrrolidineAusbeute 50 %

Versuchsvorschrift

1-[1-Benzyloxycarbonyl-4-(R)-methoxy-3-(S)-pyrrolidinyl]cyclopropanecarboxylic acid (713 mg, 2.22 mmol) was dissolved in tert-butyl alcohol (20 ml), and the solution was mixed with diphenylphosphoryl azide (623 μl, 2.89 mmol) and triethylamine (775 μl, 5.56 mmol), stirred at room temperature for 20 minutes and then heated under reflux for 19 hours. The reaction solution was cooled and then concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography and eluted with an eluant of n-hexane:ethyl acetate=3:2, to thereby obtain the title compound (431 mg, 50%) as a colorless oil.

Aufarbeitung

temperatureheated
temperatureunder reflux for 19 hours
temperatureThe reaction solution was cooled
concentrationconcentrated under reduced pressure
washeluted with an eluant of n-hexane

Quellen und Nachweise

ORD-Eintrag: ord-5f3414b9ca0a4763b5f201ffa4893e61
Quelldatensatz: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06121285

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