Water → 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

HRID 2404968ノート

反応式

HRID 2404968 の反応式
[NH2:1][C@H:2]1[C@@H:6]2[O:7][C:8]([CH3:11])([CH3:10])[O:9][C@@H:5]2[C@@H:4]([O:12][CH2:13][C:14](OCC)=[O:15])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[NH2:1][C@H:2]1[C@@H:6]2[O:7][C:8]([CH3:10])([CH3:11])[O:9][C@@H:5]2[C@@H:4]([O:12][CH2:13][CH2:14][OH:15])[CH2:3]1

参加物

5

反応物 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 70854858ethyl 2-{[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]oxy}acetate

生成物 1

HCID 99425962-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol収率 65.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of ethyl 2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)acetate (4.2 g, 16.2 mmol, 1.00 equiv.) in dry tetrahydrofuran (50 mL) was slowly added to a suspension of lithium aluminum hydride (1.23 g, 32.4 mmol, 2.00 equiv.) in tetrahydrofuran (50 mL). The mixture was heated at reflux for about 1 hour, and then water was added (2 mL). After the solids were collected by filtration, the solids were washed with tetrahydrofuran (50 mL) and then dried in vacuo to give the title product as a yellow oil (2.3 g, 65%). MS: m/z=218 (MH)+.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for about 1 hour
  3. filtrationAfter the solids were collected by filtration
  4. washthe solids were washed with tetrahydrofuran (50 mL)
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-cca83917731c4ae88525fa2e19200126
出典データセット
uspto-grants-2014_08
特許番号
US08802850B2

反応ノート

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