Triethylamine → 907608-98-4

Temperature

0 °C

To a solution of cyclopentane-1,1-dicarboxylic acid methyl ester (1.00 g, 5.81 mmol) and triethylamine (808 uL, 5.81 mmol) in THF (15 mL) is added isobutyl chloroformate (750 uL, 5.81 mmol) at 0° C. The mixture is stirred at 0° C. for 20 minutes. The mixture is filtrated, and the filtrate is added to a suspension of NaBH4 (242 mg) in THF (15 ml) at 0° C. The mixture is stirred at 0° C. for 3 hours and at room temperature for 12 hours. To the mixture, H2O is added and the mixture is extracted with AcOEt. The organic layer is dried over MgSO4, and concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography to give 1-hydroxymethyl-cyclopentanecarboxylic acid methyl ester (433 mg, 47%); TLC (hexane/AcOEt, 1:1) Rf 0.43, 1H NMR (400 MHz, chloroform-d) δ ppm 1.61-1.77 (m, 6H), 1.93-2.00 (m, 2H), 2.53 (m, 1H), 3.57 (d, 2H), 3.72 (s, 3H).

1. filtrationThe mixture is filtrated
2. additionthe filtrate is added to a suspension of NaBH4 (242 mg) in THF (15 ml) at 0° C
3. stirringThe mixture is stirred at 0° C. for 3 hours and at room temperature for 12 hours
4. additionTo the mixture, H2O is added
5. extractionthe mixture is extracted with AcOEt
6. dry with materialThe organic layer is dried over MgSO4
7. concentrationconcentrated under reduced pressure
8. customThe obtained residue is purified by silica gel column chromatography

ORD record

ord-1515738fd6d643958dcfa7780a632c16

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193349B2