Processes for the preparation of deuterated D-serine

A compound represented by the structure (E):

• wherein
• R2 is C1-C6alkyl, C3-C6cycloalkyl, or aryl;
• and
• R3 is H, D, —C(O)H, —C(O)—X—C1-C6alkyl, —C(O)—X—C3-C6cycloalkyl, —C(O)—X—CH2-aryl, —C(O)—X-aryl, or —CH2-aryl, wherein X is absent, O, NH, or S;
• wherein the compound has a deuterium incorporation of at least 90% at the position specified as deuterium.

A method for preparing a compound represented by the structure (D):

• wherein
• R1 is H, C1-C6alkyl, C3-C6cycloalkyl, —CH2-aryl, or aryl;
• R2 is C1-C6alkyl, C3-C6cycloalkyl, or aryl;
• and
• R3 is H, D, or a protecting group;
• wherein the compound has a deuterium incorporation of at least 90% at the position specified as deuterium,
• the method comprising the steps of:
• contacting a compound represented by the structure (B)
• in which R1, R2, and R3 are as defined for the compound of Formula (D);
• with a base to form a reaction mixture;
• and
• contacting the reaction mixture with at least 1 equivalent of a deuterium source;
• under conditions such that the compound of structure (D) is formed;
• wherein the compound of structure (D) has a deuterium incorporation of at least 90% at the position specified as deuterium.