Sodium hydride → 2-[(Benzyloxy)methyl]-4-tert-butylmorpholine

HRID 2371215ノート

反応式

HRID 2371215 の反応式
[CH2:1]([O:8][CH2:9][CH:10]([OH:20])[CH2:11][N:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][CH2:14]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C1(C)C=CC(S(C2NC=CN=2)(=O)=O)=CC=1>C1COCC1>[CH2:1]([O:8][CH2:9][CH:10]1[O:20][CH2:14][CH2:13][N:12]([C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 202744982-Tosyl-1H-imidazoleHCID 576568621-(Benzyloxy)-3-(tert-butyl(2-hydroxyethyl)amino)propan-2-ol

生成物 1

HCID 576569302-[(Benzyloxy)methyl]-4-tert-butylmorpholine収率 90.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1-(benzyloxy)-3-[tert-butyl(2-hydroxyethyl)amino]propan-2-ol (100 mg) in THF (20 mL) was stirred at room temperature under argon. Sodium hydride (60%, 35 mg) was added and the mixture was stirred for 2 hours. The mixture was cooled to ice bath temperature and para-toluenesulfonyl imidazole (79 mg) was added. After 30 minutes the mixture was warmed to room temperature and stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride and then partitioned between 1:1 brine/saturated aqueous sodium hydrogen carbonate and ethyl acetate. The organic layer was washed with 1:1 brine/saturated aqueous sodium hydrogen carbonate, dried (MgSO4), filtered and concentrated at reduced pressure. The residue was purified on the Isco™ Companion (12 g column: 0-10% MeOH in DCM) to give the title compound as a colourless oil (85 mg).

後処理

  1. additionwas added
  2. stirringstirred overnight
  3. customThe reaction was quenched with saturated aqueous ammonium chloride
  4. custompartitioned between 1:1 brine/saturated aqueous sodium hydrogen carbonate and ethyl acetate
  5. washThe organic layer was washed with 1:1 brine/saturated aqueous sodium hydrogen carbonate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was purified on the Isco™ Companion (12 g column: 0-10% MeOH in DCM)

出典と根拠

ORDレコード
ord-c17beb315cd740fb8e298c74c8ec9236
出典データセット
uspto-grants-2014_04
特許番号
US08710224B2

反応ノート

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