How to say while he was studying, he fell asleep. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh勉強中勉強中(benkyouchuu) (n) while studyingに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.寝(ne) (ok) sleep入ってno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbしまったしまった(shimatta) (int) damn it!/damn!/oops!/oh dear!/oh no!。(。) Japanese period "."    
kareha benkyouchuu ni ne itsutte shimatta 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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