4-Methylmorpholine → ((3As,5r,6s,6as)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanone

HRID 2206746Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2206746
[OH:1][C@H:2]1[C@@H:6]2[O:7][C:8]([CH3:11])([CH3:10])[O:9][C@@H:5]2[O:4][C@H:3]1[C:12]([OH:14])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C[N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1.N1CCOCC1>O1CCCC1>[OH:1][C@H:2]1[C@@H:6]2[O:7][C:8]([CH3:10])([CH3:11])[O:9][C@@H:5]2[O:4][C@H:3]1[C:12]([N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1)=[O:14]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 8083MorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57558238(3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carboxylic acid

Produkt 1

HCID 25207258((3As,5r,6s,6as)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholino)methanoneAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of (3aS,5R,6S,6aS)-6-Hydroxy-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxole-5-carboxylic acid (9.0 g, 44.2 mmol) and HBTU (25.1 g, 66.3 mmol, N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate) in tetrahydrofuran was added 4-methylmorpholine (7.3 mL, 66.3 mmol) at room temperature. After 1 h, morpholine (5.8 mL, 66.3 mmol) was added to the mixture at room temperature. After 12 h, the resulting mixture was filtered and the filter cake was washed with tetrahydrofuran. The filtrate was concentrated in vacuo, and the crude was purified by silica gel column chromatography to provide the title compound (5.8 g, 48%) as a yellow solid.

Aufarbeitung

  1. waitAfter 12 h
  2. filtrationthe resulting mixture was filtered
  3. washthe filter cake was washed with tetrahydrofuran
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe crude was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-51d1b647b2c5446c903eac62344524bf
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371303B2

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