Heptane → Tert-butyl 2,4-dioxo-3-oxa-7-azabicyclo[3.3.1]nonane-7-carboxylate

HRID 1475177Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]([C:14]([OH:16])=O)[CH2:11][CH:10]([C:17]([OH:19])=[O:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O.CCCCCCC>O1CCCC1>[O:16]=[C:14]1[O:19][C:17](=[O:18])[CH:10]2[CH2:11][CH:12]1[CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]2

Participants

Conditions

Temperature: 25 °C

Procedure

Under a nitrogen stream, 1-(tert-butoxycarbonyl)piperidine-3,5-dicarboxylic acid (5.00 g, 18.3 mmol) was suspended in tetrahydrofuran (10.0 mL), and trifluoroacetic anhydride (3.80 mL, 27.5 mmol) was added dropwise at 20-30° C. After completion of the dropwise addition, the mixture was stirred at 20-30° C. for 1 hr. To the reaction mixture was added dropwise heptane (20.0 mL) at 20-30° C., and the mixture was cooled to 0-10° C. and stirred for 3 hr. The precipitated crystals were collected by filtration, washed with heptane (3.00 mL), and dried under reduced pressure at 40° C. to give tert-butyl 2,4-dioxo-3-oxa-7-azabicyclo[3,3,1]nonane-7-carboxylate as a white crystalline powder (4.03 g, yield 86.1%).

Workup

additionAfter completion of the dropwise addition
temperaturethe mixture was cooled to 0-10° C.
stirringstirred for 3 hr
filtrationThe precipitated crystals were collected by filtration
washwashed with heptane (3.00 mL)
customdried under reduced pressure at 40° C.

Sources & evidence

ORD record: ord-423807f8dc6743bcb521317de26003f4
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018374B2

Reaction notes

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