ChemicalBook CAS DataBase List 3-FORMYL-MORPHOLINE-4-CARBOXYLIC ACID TERT-BUTYL ESTER

3-FORMYL-MORPHOLINE-4-CARBOXYLIC ACID TERT-BUTYL ESTER synthesis

6synthesis methods

Product Name:3-FORMYL-MORPHOLINE-4-CARBOXYLIC ACID TERT-BUTYL ESTER
CAS Number:833474-06-9
Molecular formula:C10H17NO4
Molecular Weight:215.25

473923-56-7 Synthesis

3-HYDROXYMETHYL-MORPHOLINE-4-CARBOXYLIC ACID TERT-BUTYL ESTER

473923-56-7
96 suppliers
$19.00/100mg

3-FORMYL-MORPHOLINE-4-CARBOXYLIC ACID TERT-BUTYL ESTER

833474-06-9
62 suppliers
$137.00/100mg

Yield: 84%

Reaction Conditions:

Stage #1:tert-Butyl 3-(hydroxymethyl)-4-morpholinecarboxylate with oxalyl dichloride;dimethyl sulfoxide in dichloromethane at -78; for 2.25 h;
Stage #2: with triethylamine in dichloromethane at -78 - 20; for 1.5 h;

Steps:

91
INTERMEDIATE 91fert-Butyl 3 -formylmorpholine-4-carboxylateTo a stirred solution of oxalyl chloride (3.73 g, 2.56 mL, 29.00 mmol) in DCM (80 mL) at -78⁰C was added DMSO (4.93 g, 4.47 mL, 63.00 mmol) and, after 15 minutes, a solution of Intermediate 90 (5.70 g, 26.26 mmol) in DCM (50 mL) was added. The reaction mixture was then stirred at -78⁰C for a further 2 h. NEt₃ (13.12 g, 18.71 mL, 129.70 mmol) was added and the reaction mixture was stirred at -78⁰C for 30 minutes, warmed to r.t. and stirred for a further 1 h. The reaction mixture was then concentrated in vacuo and the residue partitioned between water (200 mL) and EtOAc (200 mL). The aqueous fraction was extracted with EtOAc (2 x 200 mL) and the combined organic fractions were washed with brine (300 mL), dried (MgSO₄), filtered and the solvents removed in vacuo to give the title compound (4.80 g, 84%) as a pale yellow solid that was used crude. δ_H (CDCl₃) 9.58 (IH, s), 4.31 (2H₅ m), 3.62 (2H, br. m), 3.41 (IH, br. m), 3.11 (IH, br. s), 2.93 (IH, br. m), 1.40 (9H, s).

References:

UCB S.A. WO2006/114606, 2006, A1 Location in patent:Page/Page column 70

212650-43-6 Synthesis