Tetrahydrofuran → 2-Amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol

HRID 1802059ノート

反応式

HRID 1802059 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[NH2:12][C:13]([CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=2)[CH2:21]1)([CH3:19])[C:14](OCC)=[O:15]>C(OCC)(=O)C>[NH2:12][C:13]([CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=2)[CH2:21]1)([CH3:19])[CH2:14][OH:15]

参加物

5

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 21226445Aluminium lithium hydrideHCID 67422105Ethyl 2-amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propanoate

生成物 1

HCID 461946762-Amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol収率 49.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a 2 L flask cooled by ice water was added 60 g LiAlH4, and 1 L of THF. When the mixture was cooled to below 10° C., a mixture of 118.8 grams of ethyl 2-amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propanoate and 350 mL THF was added dropwise. No starting material remained by HPLC. The temperature was kept below 30° C. while 100 mL ethyl acetate was added. To the concentrated mixture was added 400 mL ethyl acetate, followed by 25 mL ice water. The mixture was filtered, and the filter cake with 300 mL ethyl acetate. The combined organic layers washed with brine 100 mL×2, dried with Na2SO4, decolorized with carbon and concentrated. To the oil, was added ether, the mixture stirred for overnight, filtered and dried to afford 50 g of 2-amino-2-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propan-1-ol.

後処理

  1. temperatureWhen the mixture was cooled to below 10° C.
  2. additionwas added dropwise
  3. additionwas added
  4. filtrationThe mixture was filtered
  5. washThe combined organic layers washed with brine 100 mL×2
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. additionTo the oil, was added ether
  9. filtrationfiltered
  10. customdried

出典と根拠

ORDレコード
ord-db12519908b341c0a79c7072af4520cd
出典データセット
uspto-grants-2013_01
特許番号
US08349849B2

反応ノート

読み込み中…