OPT conundrum

Hello,

My Indian friend joined Purdue University in Fall 2007. He found that having missed taking a required course, he would not be able to graduate on time at the end of Spring 2011. He traveled home to India in the summer of 2011, and as a result of a massive oversight realized that his I-20 had expired while he was on the way to the airport to fly back to the US. He returned home, and found that he would not be able to make it to Purdue in time to take said course in Fall 2011, so decided to postpone returning to Purdue/US till Fall 2012 since the course is not offered in the Spring. Then, his F-1 visa had expired by the summer of 2012, so he reapplied, but due to a clerical error, his new I-20 was mailed to the wrong address, with the result that he showed up for his visa interview without an I-20. His application was understandably denied. He has finally managed to return to Purdue now, and is on track to graduating shortly.

Now the issue is that as explained above, he is presently on a new F-1 visa and an initial I-20 and is thus unable to apply for OPT - but this seems unfortunate to me since he will be completing a full 4-year undergraduate degree from a good University and I'm quite sure he'd learn and contribute a lot during OPT. I thus welcome any advice/suggestions such that he is able to leverage one year of practical training.

Thanking you in anticipation.