Benzyl Alcohol → Benzyl (3-oxocyclobutyl)carbamate

HRID 511608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511608
[O:1]=[C:2]1[CH2:5][CH:4](C(O)=O)[CH2:3]1.CC[N:11]([CH:15](C)C)C(C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])=CC=1.[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1(C)C=CC=CC=1>[O:1]=[C:2]1[CH2:3][CH:4]([NH:11][C:15](=[O:25])[O:42][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:5]1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 49133583-Oxocyclobutane-1-carboxylic acid

Produkt 1

HCID 19794323Benzyl (3-oxocyclobutyl)carbamateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3-oxocyclobutanecarboxylic acid (1.0 g, 8.77 mmol) and DIEA (1.92 g, 14.92 mmol) in toluene (8 mL) was added DPPA (2.89 g, 10.52 mmol) at rt. The mixture was heated to 60° C. under Argon for 3 h, then benzyl alcohol (1.14 g, 10.52 mmol) was added. The mixture was stirred at 60° C. overnight. The reaction was concentrated, the residue was purified by SGC (PE:EA=8:1) to afford the desired compound (240 mg, yield 50%). 1H NMR (500 MHz, CDCl3): δH 7.38-7.33 (m, 5H), 5.12 (d, J=7.5 Hz, 2H), 4.34-4.33 (brs, 1H), 3.44-3.39 (m, 2H), 3.10-3.07 (brs, 2H) ppm; ESI-MS (m/z): 220.2 [M+1]+.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified by SGC (PE:EA=8:1)

Quellen und Nachweise

ORD-Eintrag
ord-56bdcebd2c844aebba11c53a4cf5e8a8
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096634B2

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