Water → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 1383393Notes

Reaction equation

[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].O>CS(C)=O>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][C:19]2([O:22][CH2:4]2)[CH2:20][CH2:21]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 62.5 °C

Procedure

Oil free sodium hydride (2.16 g, 0.09 M) was added to dry dimethyl sulfoxide (250 mL) under nitrogen gas and the mixture was heated to 60-65° C. until a uniform black solution was formed, about 1 h. Then 19.83 g (0.09 M) of trimethylsulfoxonium iodide was added (slight exotherm) and the mixture was stirred until a brown solution occurred, about 30 min. Then a solution of 13.40 g (67.3 mM) of N-t-butyloxycarbonyl-4-piperidone in 50 mL of dimethyl sulfoxide was stirred at room temperature for 1 h. The reaction mixture was then poured into 1 L of cold water and the whole was extracted 4× with 100 mL portions of hexane. The combined hexane extracts was back-washed with 50 mL of water and with brine solution and was dried with magnesium sulfate, filtered and evaporated to give 11.75 g of white crystalline product, 6-t-butyloxycarbonyl-1-oxa-6-azaspiro[2.5]octane, (78% yield).

Workup

customwas formed, about 1 h
extractionthe whole was extracted 4× with 100 mL portions of hexane
washThe combined hexane extracts was back-washed with 50 mL of water and with brine solution
dry with materialwas dried with magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-d34a80eb76174680b969759b45d38757
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255322B1

Reaction notes

Loading…