ChemicalBook CAS DataBase List 4-Hydroxybutanoic acid methyl ester

4-Hydroxybutanoic acid methyl ester synthesis

12synthesis methods

Product Name:4-Hydroxybutanoic acid methyl ester
CAS Number:925-57-5
Molecular formula:C5H10O3
Molecular Weight:118.13

3878-55-5 Synthesis

3878-55-5
250 suppliers
$9.00/1g

543-27-1
260 suppliers
$10.00/5g

925-57-5
47 suppliers
$70.00/100mg

Yield:-

Reaction Conditions:

Stage #1:methyl hydrogen succinate;isobutyl chloroformate with triethylamine in tetrahydrofuran at 0; for 0.5 h;
Stage #2: with sodium tetrahydroborate in water at 18 - 22; for 2 h;

Steps:

15.1 Preparation of intermediate 15a
A solution of mono-methyl succinate (2.0 g, 15.1 mmol, Aldrich) in THF (30.0 mL) is cooled to 000 and TEA (2.2 mL, 15.7 mmol) followed by isobutyl chloroformate (2.05 g, 15.0 mmol) areadded. The resulting mixture is stirred at 0°C for 30 minutes. The resulting residue is filtered on Millex and directly added to a solution of NaBH4 (1.15 g, 30.4 mmol) in 20 mL of water. The reaction is stirred for 2 hours at RT. The mixture is diluted with water, acidified with a 1 N solution of HCI and extracted twice with EtOAc. The organic layers are combined, washed with brine, dried over MgSO4, filtered and concentrated. The crude product is purified by Combif lash (50:50 Hex/EtOAc) to afford iSa.

References:

MEDIVIR AB;BROCHU, Christian;DECOR, Anne;GHIRO, Elise;PESANT, Marc;KUHN, Cyrille WO2015/65336, 2015, A1 Location in patent:Page/Page column 31

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