1H-3a,7-Methanoazulen-5(4H)-one, hexahydro-3,6,8,8-tetramethyl- → HCID 70926346, compound

HRID 1042416Notes

Reaction equation

HRID 1042416 reaction equation
[CH3:1][CH:2]1[C:11]23[CH2:12][CH:7]([CH:8]([CH3:14])[C:9](=O)[CH2:10]2)[C:6]([CH3:16])([CH3:15])[CH:5]3[CH2:4][CH2:3]1.[C:17](O)(=O)C.[CH:21]([NH2:23])=[NH:22]>C(O)CCC>[CH3:14][CH:8]1[C:9]2=[N:22][CH:21]=[N:23][CH:17]=[C:10]2[C:11]23[CH2:12][CH:7]1[C:6]([CH3:16])([CH3:15])[CH:5]2[CH2:4][CH2:3][CH:2]3[CH3:1]

Participants

4

Reactant 2

HCID 1114021H-3a,7-Methanoazulen-5(4H)-one, hexahydro-3,6,8,8-tetramethyl-HCID 160693Formamidine acetate

Product 1

HCID 70926346HCID 70926346, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
130 °C

Procedure

A 100 mL reaction flask is charged with 3,6,8,8-tetramethyl-hexahydro-3a,7-methano-azulen-5-one (prepared as described in U.S. Pat. No. 3,887,622) (10 g, 0.045 mol), formamidine acetate (21 g, 0.2 mol), and butanol (50 mL). The reaction mixture is heated to 130° C. and stirred for 24 hours. The crude mass is washed once with aqueous sulfuric acid (10%, 100 mL) followed by twice with brine (30 mL). Butanol is recovered by roto-evaporation. The crude product is further purified with liquid chromatography (Biotage® system) and then crystallized. Product 5,7,7,10-tetramethyl-6,7,7a, 8,9,10-hexahydro-5H-6,10a-methanoazuleno[5,4-d]pyrimidine (˜5 g) is obtained.

Workup

  1. customA 100 mL reaction flask
  2. customprepared
  3. washThe crude mass is washed once with aqueous sulfuric acid (10%, 100 mL)
  4. customButanol is recovered by roto-evaporation
  5. customThe crude product is further purified with liquid chromatography (Biotage® system)
  6. customcrystallized

Sources & evidence

ORD record
ord-0af6375fecfe4fd2a8462b0e791e64b9
Source dataset
uspto-grants-2013_10
Patent number
US08557876B2

Reaction notes

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