It looks to me like you need the openssl libraries. Normally I would 'sudo apt install libssl-dev' and you should be able to do a similar thing with brew. brew install openssl or brew install openssl@1.1.
Try this:
brew install openssl@1.1
cpusr/local/opt/openssl@1.1/lib/pkgconfig/*.pcusr/local/lib/pkgconfig/
Hopefully that will help move things along.
bitcoinforktech is correct, you are missing the OpenSSL library on Mac which is why the pip installation fails with "cannot find <openssl/aes.h>" (last image). You need to use brew to install it.
If you don't currently have brew, you can install it using:
/bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"
Are you sure you can/cannot convert the key to WIF or somesuch and import it?
He said his private key is 66 characters long and begins with ef, while bitcoin private keys are supposed to be 64 hex characters long. It is already out of range of a valid private key:
0x1 to 0xFFFF FFFF FFFF FFFF FFFF FFFF FFFF FFFE BAAE DCE6 AF48 A03B BFD2 5E8C D036 4140
The blockstack JSON he posted suggests that this could be a master private key, but those are also 64 hex characters long and begin with xprv, but this hex number doesn't have either of these properties.
You are getting permission denied because you aren't running brew as Administrator, try running the brew install command with sudo.
@21XO, I think I asked you in your other thread what kind of address is this private key for, but I never got an answer AFAIK. Are you trying to recover a legacy address, or a segwit address?