What type of reaction is occuring in step 3? (halogenation, hydrohalogenation, reduction, keto–enol tautomerism, dehydrohalogenation, acid-catalyzed hydration, base-catalyzed hydration) 2. Which reagent is necessary for step 3? (Br2, HBr, H2/Pt, NaNH2, H20/H2SO4/HgSO4)

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1. What type of reaction is occuring in step 3? (halogenation, hydrohalogenation, reduction, keto–enol tautomerism, dehydrohalogenation, acid-catalyzed hydration, base-catalyzed hydration)

2. Which reagent is necessary for step 3? (Br2, HBr, H2/Pt, NaNH2, H20/H2SO4/HgSO4)

**Synthesis of Rimantadine from Adamantane**

*Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence:*

1. **Adamantane** is reacted with bromine (Br2) to produce **1-bromoadamantane**. This is shown as:
   - **Adamantane** + Br2 → **1-bromoadamantane** (Step 1)

2. **1-bromoadamantane** is then reacted with **AlBr3** (aluminum bromide) in the presence of **CH2=CHBr** to yield a compound with a newly formed carbon-bromine bond. This is:
   - **1-Bromoadamantane** + AlBr3 + CH2=CHBr → Intermediate (Step 2)

3. The intermediate undergoes further transformation to replace the newly added bromine atom, forming a carbon-carbon triple bond product.

4. The intermediate product is then converted to a carbonyl compound. 

5. Finally, the carbonyl compound is converted into **Rimantadine** by the introduction of an amino group (NH2). This is:
   - Intermediate + chemical transformation → **Rimantadine** (Step 5)

**Diagrams:**
- The diagrams illustrate the molecular structures at each step of the synthesis. Solid arrows indicate the progression of each synthetic step.
Transcribed Image Text:**Synthesis of Rimantadine from Adamantane** *Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence:* 1. **Adamantane** is reacted with bromine (Br2) to produce **1-bromoadamantane**. This is shown as: - **Adamantane** + Br2 → **1-bromoadamantane** (Step 1) 2. **1-bromoadamantane** is then reacted with **AlBr3** (aluminum bromide) in the presence of **CH2=CHBr** to yield a compound with a newly formed carbon-bromine bond. This is: - **1-Bromoadamantane** + AlBr3 + CH2=CHBr → Intermediate (Step 2) 3. The intermediate undergoes further transformation to replace the newly added bromine atom, forming a carbon-carbon triple bond product. 4. The intermediate product is then converted to a carbonyl compound. 5. Finally, the carbonyl compound is converted into **Rimantadine** by the introduction of an amino group (NH2). This is: - Intermediate + chemical transformation → **Rimantadine** (Step 5) **Diagrams:** - The diagrams illustrate the molecular structures at each step of the synthesis. Solid arrows indicate the progression of each synthetic step.
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