Dimethylformamide → (+/-)Tert-butyl 7-formyl-8-azaspiro[4.5]decane-8-carboxylate

HRID 536593Notes

Reaction equation

[CH2:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.CN(C)CCN(C)C.CCCCCC.CN(C)[CH:34]=[O:35].[NH4+].[Cl-]>CCOCC>[CH:34]([CH:7]1[N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][C:5]2([CH2:1][CH2:2][CH2:3][CH2:4]2)[CH2:6]1)=[O:35]

Participants

Conditions

Temperature: -78 °C

Procedure

tert-butyl 8-azaspiro[4.5]decane-8-carboxylate (Intermediate 71, 6 g, 25.07 mmol) dissolved in 150 ml of Et2O was cooled to −78° C., then N,N,N′,N′-tetramethyl ethylendiamine (9.08 ml, 60.16 mmol) and secBuLi 1.4M in hexane (42.95 ml, 60.16 mmol) were added. After 10 minutes at −60° C., the temperature was raised to −20° C. for 60 minutes, then the reaction was cooled to −78° C. and dimethylformamide (4.47 ml, 60.16 mmol, dissolved in 5 ml of Et2O) was added. After 30 minutes a saturated aqueous solution of NH4Cl (30 ml) was slowly added, then reaction was allowed to reach room temperature. Reaction was extracted with Et2O (3×100 ml), the organic solvent was dried (Na2SO4) and evaporated to obtain 4 g of the title compound as yellow oil.

Workup

temperaturethe temperature was raised to −20° C. for 60 minutes
temperaturethe reaction was cooled to −78° C.
customreaction
customto reach room temperature
customReaction
extractionwas extracted with Et2O (3×100 ml)
dry with materialthe organic solvent was dried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-82da4e89ad1748b0af2a62cfae2c75d7
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859608B2

Reaction notes

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