(S)-1-Amino-2-hydroxymethylindoline

2-hydroxymethylindoline is resolved with (S)-(+)-Mandelic Acid to give (S)-(+)-2- hydroxymethylindoline, which is then nitrosated and reduced to produce (S)-1-Amino-2-hydroxymethylindoline (eq 1).  (R)-1-Amino-2-hydroxymethylindoline is also available by a similar procedure.

(S)-1-Amino-2-hydroxymethylindoline is very air sensitive. Store under nitrogen or argon at -20 °C. Use in a fume hood.