Water → (2R)-3-(benzyloxy)-2-(tritylamino)propan-1-ol

HRID 221569ノート

反応式

HRID 221569 の反応式
[CH2:1]([O:8][CH2:9][C@@H:10]([C:31](OC)=[O:32])[NH:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH2:1]([O:8][CH2:9][C@H:10]([NH:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:31][OH:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67156483methyl O-benzyl-N-trityl-L-serinate

生成物 1

HCID 67156691(2R)-3-(benzyloxy)-2-(tritylamino)propan-1-ol収率 100.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

Methyl O-benzyl-N-trityl-L-serinate (2.94 g, 6.52 mmol) was dissolved in 100 mL of anhydrous Et2O and the solution was cooled to 0° C. under N2. Lithium aluminum hydride (1.63 g, 42.9 mmol) was added and the mixture was stirred for 90 minutes. The reaction mixture was then sequentially treated with 1.63 mL of H2O, 1.63 mL of 15% NaOH solution and 4.90 mL of H2O. After stirring for 30 minutes, the reaction mixture was filtered to remove the white solid. The solid was washed with several portions of Et2O and the combined filtrates were concentrated under reduced pressure. Chromatography (SiO2, 15-20% ethyl acetate/hexanes) gave 2.78 g of (2R)-3-(benzyloxy)-2-(tritylamino)propan-1-ol as a colorless oil.

後処理

  1. stirringAfter stirring for 30 minutes
  2. filtrationthe reaction mixture was filtered
  3. customto remove the white solid
  4. washThe solid was washed with several portions of Et2O
  5. concentrationthe combined filtrates were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-a93f7366cfac42a7ba5ae2f28c6774b4
出典データセット
uspto-grants-2012_06
特許番号
US08207162B2

反応ノート

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