At night time try to get him to bed before you are going yourself. Remember the saying a warm hello and a cold goodbye. Too much exciting stimulation before bedtime may make him too alert and not want to settle down. About half an hour before bedtime take him outside and allow him to empty his bowels. Stay out with him until he does - if you just put him outside and close the door on him he might take fright and hang around the doorstep till you let him in and then dirty in the house. When you put him into his crate put a sheet or blanket over the top of it (leaving one side uncovered if necessary but not where he can see you coming and going). Some puppies find comfort if an alarm clock (alarm turned off of course) is left near the crate or wrapped up in a blanket in the crate. I also give them a teddy bear to snuggle into. If he starts to cry do not tell him off as this may teach him that bad behaviour gets him attention. Tap the top of the crate (do not let him see you) and when he stops crying leave him a minute then quietly tell him 'good boy settle'. Sometimes if you stay at the kitchen door and bang the door, rather than go into the kitchen, this works as efficiently. Getting him used to being in the crate for periods during the day while you are around should make the bedtime routine much easier.