Diisobutylaluminum hydride → 2-Methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanal
Reaction equation
[CH3:1][C:2]([N:9]1[CH2:19][CH2:18][C:12]2([C:16](=[O:17])[NH:15][CH2:14][CH2:13]2)[CH2:11][CH2:10]1)([CH3:8])[C:3](OCC)=[O:4].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:8][C:2]([N:9]1[CH2:19][CH2:18][C:12]2([C:16](=[O:17])[NH:15][CH2:14][CH2:13]2)[CH2:11][CH2:10]1)([CH3:1])[CH:3]=[O:4]Participants
4
Procedure
To a solution of ethyl 2-methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanoate (3.77 g, 14.1 mmol) in toluene (100 mL) at −78° C. was added DIBAL-H (45.0 mL, 45.0 mmol) dropwise. After 2 h, the reaction was quenched by addition of methanol (10 mL) dropwise, after warmed to rt, 30 mL of saturated sodium sulfate solution was added and the mixture was vigorously stirred at rt for 1 h. After filtration, the filtrate and the filter cake were partitioned between DCM and saturated sodium bicarbonate, the alkaline phase was extracted with DCM three times, the combined organic phase was dried over sodium sulfate, concentrated to give the title compound. LC/MS (M+1+18)+: 243.3; (M+1+32)+: 257.4.
Workup
- customthe reaction was quenched by addition of methanol (10 mL) dropwise
- addition30 mL of saturated sodium sulfate solution was added
- filtrationAfter filtration
- customthe filtrate and the filter cake were partitioned between DCM and saturated sodium bicarbonate
- extractionthe alkaline phase was extracted with DCM three times
- dry with materialthe combined organic phase was dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ca6c5b579abc4513a7f9b098cb2039d0
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952166B2
Reaction notes
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