Acetaldehyde → Tert-butyl 3-(1-hydroxyethyl)-4-oxo-8-azaspiro[4.5]decane-8-carboxylate

HRID 8752

Reaction equation

[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3]1.[O:19]1CC[CH2:21][CH2:20]1.C([N-]C(C)C)(C)C.[Li+].C(=O)C.[Cl-].[NH4+]>C(OCC)C>[OH:19][CH:20]([CH:3]1[CH2:4][CH2:5][C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]2)[C:2]1=[O:1])[CH3:21]

Participants

Conditions

Temperature: -78 °C

Procedure

tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (1.2 g, 4.70 mmol) was dried by evaporating with toluene (5 mL) three times in vacuo, dissolved in tetrahydrofuran (50 mL), and cooled to −78° C. To this solution was added lithium diisopropylamide mono(tetrahydrofuran) (6.3 mL, 9.4 mmol, 1.5 M in cyclohexane). The reaction mixture was stirred for 35 min at −78° C. before adding acetaldehyde (0.527 mL, 9.4 mmol). After 10 min, the reaction mixture was diluted with diethyl ether, poured into saturated ammonium chloride, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 6.7 g of a clear oil. The residue was purified by flash chromatography eluting with 20–40% ethyl acetate/hexanes to give the title compound (0.620 g).

Workup

customby evaporating with toluene (5 mL) three times in vacuo
dissolutiondissolved in tetrahydrofuran (50 mL)
waitAfter 10 min
extractionextracted three times with diethyl ether
washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-0c06c86d3f3444378259f57ae88f4d91
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091211B2

Linked notes

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