Diisobutylaluminum hydride → 2-Methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanal

HRID 1848554ノート

反応式

HRID 1848554 の反応式
[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]

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 86709536Ethyl 2-methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanoate

生成物 1

HCID 867095372-Methyl-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)propanal

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  1. customthe reaction was quenched by addition of methanol (10 mL) dropwise
  2. addition30 mL of saturated sodium sulfate solution was added
  3. filtrationAfter filtration
  4. customthe filtrate and the filter cake were partitioned between DCM and saturated sodium bicarbonate
  5. extractionthe alkaline phase was extracted with DCM three times
  6. dry with materialthe combined organic phase was dried over sodium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ca6c5b579abc4513a7f9b098cb2039d0
出典データセット
uspto-grants-2015_02
特許番号
US08952166B2

反応ノート

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