Triphenylphosphine → Di-tert-butyl 1-(cyclopropylmethyl)hydrazine-1,2-dicarboxylate

HRID 536708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536708
[CH:1]1([CH2:4]O)[CH2:3][CH2:2]1.[NH:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)(C)C)=O)=N\C(OC(C)(C)C)=O>C1COCC1>[CH:1]1([CH2:4][N:6]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 85431Di-tert-butyl bicarbamateHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylate

Produkt 1

HCID 66643119Di-tert-butyl 1-(cyclopropylmethyl)hydrazine-1,2-dicarboxylateAusbeute 354,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of cyclopropylmethanol (7.15 mL, 90 mmol), di-tert-butyl hydrazine-1,2-dicarboxylate (6.30 g, 27.1 mmol) and triphenylphosphine (28.5 g, 109 mmol) in THF (100 mL) was added (E)-di-tert-butyl diazene-1,2-dicarboxylate (25 g, 109 mmol) in portions at ambient temperature. The reaction mixture was concentrated and allowed to stand overnight. The white solid (PPh3O) precipitated was filtered off and the filtrate was purified by flash chromatography (silica gel, EtOAc in Hexane in 5-25% gradient) to yield 27.5 g (96%) of the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. customThe white solid (PPh3O) precipitated
  3. filtrationwas filtered off
  4. customthe filtrate was purified by flash chromatography (silica gel, EtOAc in Hexane in 5-25% gradient)

Quellen und Nachweise

ORD-Eintrag
ord-2316340816cb4158a2fdf9fa21d25c48
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859596B2

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