Not with that type of med but I did have a big struggle with giving my daughter a swallow-able pill for the first time. She was screaming, gagging, crying. I tried mincing it up and putting it in peanut butter or something she may like and it just had it horrible tasting. It was a strong tasting pill. Her dad was there to help and after nearly half an hour she calmed down enough for her dad to coach her on it. Once she did it she was like, "Oh! That's not that bad." Too funny. After that she prefers pills. It makes her feel less babyish and she doesn't have to taste the medicine. She's taken some horse pills and those can be harder to swallow. The best place to put the pill is underneath the tongue beside the molars.
If it gets too complicated for him, then talk with the doctor about seeing if you can get the prescription in smaller pills. I don't know why pharmacists expect people to swallow hockey pucks.