Diphenylsilane → (S)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate

HRID 1476314

Reaktionsgleichung

Reaktionsgleichung von HRID 1476314
[C:1]([NH:4][CH2:5][C@H:6]1[CH2:11][O:10][CH2:9][CH2:8][N:7]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)[CH3:2].[C:19]1([SiH2]C2C=CC=CC=2)C=CC=C[CH:20]=1>O1CCCC1.[C-]#[O+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Rh]>[CH2:1]([N:4]([CH2:5][C@H:6]1[CH2:11][O:10][CH2:9][CH2:8][N:7]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:19][CH3:20])[CH3:2]

Komponenten

5

Edukt 2

HCID 69888DiphenylsilaneHCID 66723613(S)-tert-butyl 3-(acetamidomethyl)morpholine-4-carboxylate2×

Produkt 1

HCID 66723823(S)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10941995Carbonylhydridotris(triphenylphosphine)rhodium(I)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl 3-((N-ethylacetamido)methyl)morpholine-4-carboxylate (INTERMEDIATE 86A, Step 2, 0.04 g, 0.14 mmol) and diphenylsilane (0.052 ml, 0.28 mmol) in tetrahydrofuran (1.345 ml) at rt was added carbonyltris(triphenylphosphine)rhodium(I) hydride (6.42 mg, 6.98 μmol). After a brief surge of gas evolution, the now yellow reaction was stirred for 30 min and then quenched with 1N aqueous hydrogen chloride. The mixture was extracted with ether, and the aqueous layer was basified with 50% aqueous sodium hydroxide. The aqueous layer was the extracted with ethyl acetate (×4), and the combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford (S)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate (0.038 g, yield: almost quantitative) (INTERMEDIATE 86A, Step 3).

Aufarbeitung

  1. customAfter a brief surge of gas evolution, the now yellow reaction
  2. customquenched with 1N aqueous hydrogen chloride
  3. extractionThe mixture was extracted with ether
  4. extractionextracted with ethyl acetate (×4)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a15014b147ff4883b7a360225145941d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018381B2

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