Ethyl Acetate → N-benzyl-2-(2-fluoro-3-methyl-benzyl)-morpholine

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Potassium Sodium Tartrate	HCID 9357	—
Reactant	N-Boc-(R)-2-(3-(hydroxymethyl)benzyl)morpholine	HCID 67073062	—
Reactant	N-benzyl-2-(2-Fluoro-3-methyl-benzyl)-morpholin-3-one	HCID 67073236	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-benzyl-2-(2-fluoro-3-methyl-benzyl)-morpholine	HCID 67073026	—
Product	N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine	HCID 67073511	—

Reaction Conditions

Temperature	23 °C

Reaction Steps

To a solution of intermediate (b), N-benzyl-2-(2-Fluoro-3-methyl-benzyl)-morpholin-3-one (275 mg, 0.876 mmol) in tetrahydrofuran (10 mL) at 0° C. was added BH3 (1M in tetrahydrofuran, 2.63 mL, 2.63 mmol). The mixture was stirred at 23° C. for 1 h then heated to reflux for 18 h, cooled to 23° C. and stirred vigorously with Rochelle's salt solution (15 mL) for 1.5 h. Ethyl acetate (30 mL) was added and stirring continued for 1.5 h. The organic phase was separated, dried (Na2SO4) and concentrated affording intermediate (a), N-benzyl-2-(2-fluoro-3-methyl-benzyl)-morpholine, as a pale yellow oil (190 mg, 73%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07323466B2
Source dataset	uspto-grants-2008_01
ORD ID	ord-cfc18c548e40431cbd4e103daca7a5dd
Source note	uspto-grants-2008_01