Lithium Hydroxide → Tert-butyl 1-oxo-8-azaspiro(4.5)decane-8-carboxylate

HRID 8749

Reaction equation

COC([CH:5]1[CH2:9][CH2:8][C:7]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[C:6]1=[O:22])=O.[OH-].[Li+]>C(O)C.O1CCCC1.O>[O:22]=[C:6]1[C:7]2([CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)[CH2:8][CH2:9][CH2:5]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of tert-butyl 2-(methoxycarbonyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate (17.2 g, 0.055 mol) from Step F in a 2:2:1 mixture of ethanol/tetrahydrofuran/water (555 mL) was added pulverized lithium hydroxide (26 g, 1.10 mol). The reaction mixture was heated to 90° C. for 60 h. The reaction mixture was allowed to cool and was then concentrated, dissolved in water and dichloromethane, and extracted three times with dichloromethane. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 11.4 g. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (9.41 g).

Workup

additionwas added
temperatureto cool
concentrationwas then concentrated
dissolutiondissolved in water
extractiondichloromethane, and extracted three times with dichloromethane
washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customto afford 11.4 g
customThe residue was purified by flash chromatography
washeluting with 20–30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-279bb325608143949a9c5045f8750794
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091211B2

Linked notes

Loading…