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

HRID 1022466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022466
[OH:1][C@H:2]1[C@H:9]2[C@H:5]([O:6][C:7]([CH3:11])([CH3:10])[O:8]2)[O:4][C@H:3]1[C:12]([OH:14])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C[N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.N1CCOCC1>C1COCC1>[OH:1][C@H:2]1[C@H:9]2[C@H:5]([O:6][C:7]([CH3:10])([CH3:11])[O:8]2)[O:4][C@H:3]1[C:12]([N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)=[O:14]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 8083MorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 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 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Step-IV: To a stirred solution of (3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid (20 g, 98 mmol) in THF (400 ml) was added TBTU (47.2 g, 147 mmol), N-methylmorpholine (NMM, 16.16 ml, 147 mmol) at room temperature and stirred for 30 min. To it was added morpholine (12.99 ml, 147 mmol) and stirred for 6 h. The solid was filtered off by filtration and it was washed with THF. The filtrate was concentrated and resulting residue was purified by silica gel column chromatography to give 17.8 g of ((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-morpholin-4-yl-methanone as a white solid. 1H NMR (400 MHz, CD3OD): δ 1.33 (s, 3H), 1.49 (s, 3H), 3.42-3.53 (m, 2H), 3.62-3.83 (m, 6H), 4.47 (d, J=2.0 Hz, 1H), 4.57 (d, J=3.6 Hz, 1H), 4.59 (d, J=2.0 Hz, 1H), 6.00 (d, J=3.2 Hz, 1H).

Aufarbeitung

  1. stirringstirred for 6 h
  2. filtrationThe solid was filtered off by filtration and it
  3. washwas washed with THF
  4. concentrationThe filtrate was concentrated
  5. customresulting residue
  6. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dd05257cb55147708fb2d5d44aa58ec6
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722633B2

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