ethyl 2-[(4-chlorophenyl)methylamino]acetate

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of glycine ethyl ester hydrochloride (1.2 eq.) in DCE was added TEA (2 eq.) The reaction was stirred for 10 min at 20° C. then 4-chlorobenzaldehyde (1 eq.), acetic acid (4 eq.) and sodium triacetoxyborohydride (2 eq.) were added. The reaction was stirred for 15 h at 20° C. The crude was partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous layer was then extracted twice with DCM. The organic layers were combined, washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to afford (4-chloro-benzylamino)-acetic acid ethyl ester. The reaction was stirred for 15 h at 20° C The crude was partitioned between DCM The aqueous layer was then extracted twice with DCM washed with brine dried on MgSO4 filtered concentrated under reduced pressure

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of glycine ethyl ester hydrochloride (1.2 eq.) in DCE was added TEA (2 eq.) The reaction was stirred for 10 min at 20° C. then 4-chlorobenzaldehyde (1 eq.), acetic acid (4 eq.) and sodium triacetoxyborohydride (2 eq.) were added. The reaction was stirred for 15 h at 20° C. The crude was partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous layer was then extracted twice with DCM. The organic layers were combined, washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to afford (4-chloro-benzylamino)-acetic acid ethyl ester. The reaction was stirred for 15 h at 20° C The crude was partitioned between DCM The aqueous layer was then extracted twice with DCM washed with brine dried on MgSO4 filtered concentrated under reduced pressure

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of glycine ethyl ester hydrochloride (1.2 eq.) in DCE was added TEA (2 eq.) The reaction was stirred for 10 min at 20° C. then 4-chlorobenzaldehyde (1 eq.), acetic acid (4 eq.) and sodium triacetoxyborohydride (2 eq.) were added. The reaction was stirred for 15 h at 20° C. The crude was partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous layer was then extracted twice with DCM. The organic layers were combined, washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to afford (4-chloro-benzylamino)-acetic acid ethyl ester. The reaction was stirred for 15 h at 20° C The crude was partitioned between DCM The aqueous layer was then extracted twice with DCM washed with brine dried on MgSO4 filtered concentrated under reduced pressure

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of glycine ethyl ester hydrochloride (1.2 eq.) in DCE was added TEA (2 eq.) The reaction was stirred for 10 min at 20° C. then 4-chlorobenzaldehyde (1 eq.), acetic acid (4 eq.) and sodium triacetoxyborohydride (2 eq.) were added. The reaction was stirred for 15 h at 20° C. The crude was partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous layer was then extracted twice with DCM. The organic layers were combined, washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to afford (4-chloro-benzylamino)-acetic acid ethyl ester. The reaction was stirred for 15 h at 20° C The crude was partitioned between DCM The aqueous layer was then extracted twice with DCM washed with brine dried on MgSO4 filtered concentrated under reduced pressure