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

HRID 1771209

反応式

HRID 1771209 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 53249357Carbonyltris(triphenylphosphine)rhodium(I)hydride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 mol). 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).

後処理

  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

出典と根拠

ORDレコード
ord-1007ede46448424a868285284aefc8b5
出典データセット
uspto-grants-2016_02
特許番号
US09248140B2

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