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

HRID 1759540노트

반응식

HRID 1759540 반응식
[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

참가 물질

4

반응물 3

HCID 222Ammonia2회HCID 962WaterHCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane

생성물 1

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

반응 조건

온도
-70 °C

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-9dd463ef16eb4658ba8456954ffafde4
출처 데이터셋
uspto-grants-1982_07
특허 번호
US04341756

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