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I was bored the other day and got to thinking about putting a 3 or 4 cylinder 2 stroke detroit diesel in a 1950 3100. What would be transmission options? It is only a 2wd but i was thinking of finding an axle of a 70s 4x4 and fabbing that up and using it. If I did take that route what would be a good transfer case? And what engine would fit the best?

Best fit, 3-53 or even 2-53
Best bang for the buck, 3-53T.

Transmission, probably overdrive unless you choose a rear axle with some very fast ratios available.
A 6 speed would be nice for the closer spaced ratios.

Easier fit is special two piece flywheel housing and flywheel Detroit offered for conversion in trucks years ago, two sizes of GM housings. The small one fits angled rear engine mounts in 1954 and later small trucks, standard transmission pattern same as SM420.
Larger GM housing fits angled rear mounts in larger size trucks same time period, same transmissions fit and also Spicer 3000 series (has dual pattern).

No input on 4x4, probably more trouble than it’s worth.

Grigg

My wife's 64 Ford fishing truck had a 4 cylinder Perkins diesel in it when I bought it and it was not a good combination. Probably the biggest mistake was using a half ton and the gearing was wrong. Traded the Perkins even to a salvage yard for a 302/C4 set up and we were both happy.

Detroit 2 stroke engines need gears- - - - -lots of them- - - - -since the effective torque band is so narrow. You'll need a gear for every 400 RPM since the useful torque range is from 1750-2150. They're also HEAVY, so anything less than a 1 ton truck is probably going to be extremely nose-heavy and the front wheel bearings and springs are probably going to be overloaded. After everything is sorted out and working, you'll have a noisy, stinky, heavy, slow truck you have to row with the shift lever(s). Have fun, but that sounds like a masochist's pipe dream!
Jerry