Ammonia → (5S,6R)-6-amino-2,2-dimethyl-1,3-dioxepan-5-ol

HRID 1904067ノート

反応式

HRID 1904067 の反応式
[CH3:1][C:2]1([CH3:10])[O:9][CH2:8][CH:7]2[CH:5]([O:6]2)[CH2:4][O:3]1.O.[NH3:12]>>[CH3:1][C:2]1([CH3:10])[O:9][CH2:8][C@@H:7]([NH2:12])[C@H:5]([OH:6])[CH2:4][O:3]1

参加物

4

反応物 3

HCID 222Ammonia2 回HCID 962WaterHCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

生成物 1

HCID 58287017(5S,6R)-6-amino-2,2-dimethyl-1,3-dioxepan-5-ol収率 87%

反応条件

温度
-70 °C

実験手順

A steel bomb was charged with liquid ammonia (60 ml) with cooling in an isopropanol-dry ice bath maintained at -70° C. The epoxide (III) (21.46 g, 0.15 mole) was added to it, followed by water (2.70 ml, 0.15 mole). The bomb was sealed and, then, heated in an oil bath at 120° for 4 hr. The bomb was cooled, opened and the ammonia was allowed to evaporate. The crude residue was triturated with ether, chilled, and the crystalline product was isolated by filtration. The amine (IV) was obtained as white prisms. (18.78 g, yield 87%). m.p. 81.5°-82.5°.

後処理

  1. temperaturewith cooling in an isopropanol-dry ice bath
  2. customThe bomb was sealed
  3. temperatureheated in an oil bath at 120° for 4 hr
  4. temperatureThe bomb was cooled
  5. customto evaporate
  6. customThe crude residue was triturated with ether
  7. temperaturechilled
  8. customthe crystalline product was isolated by filtration

出典と根拠

ORDレコード
ord-db2f99143d6546f2bcb9e11aace1ff70
出典データセット
uspto-grants-1984_03
特許番号
US04439613

反応ノート

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