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

HRID 1904067Notes

Reaction equation

HRID 1904067 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
-70 °C

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-db2f99143d6546f2bcb9e11aace1ff70
Source dataset
uspto-grants-1984_03
Patent number
US04439613

Reaction notes

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