Diisopropylamine → 8-Benzyl-3-oxa-1,8-diazaspiro[4.5]decan-2-one

HRID 385779ノート

反応式

HRID 385779 の反応式
[NH2:1][C:2]1([CH2:15][OH:16])[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C(NC(C)C)(C)C.Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl.[NH4+].[OH-]>C1(C)C=CC=CC=1.O>[CH2:8]([N:5]1[CH2:6][CH2:7][C:2]2([NH:1][C:25](=[O:27])[O:16][CH2:15]2)[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 14923Ammonium HydroxideHCID 94429TriphosgeneHCID 22020939HCID 22020939、化合物

生成物 1

HCID 577809438-Benzyl-3-oxa-1,8-diazaspiro[4.5]decan-2-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
0 °C

実験手順

To a 1 L 4-neck round bottom flask was added (4-amino-1-benzylpiperidin-4-yl)methanol (21.86 g, 99 mmol) and diisopropyl amine (23.0 g, 249 mmol) in dry toluene (300 ml). The reaction mixture was cooled to 0° C. and a solution of triphosgene (35.57 g, 119 mmol) in toluene (100 ml) was added. The reaction mixture was heated to 60° C. for 1.5 h. After cooling to room temperature, the reaction mixture was diluted with water (200 ml), basified with aqueous NH4OH, and extracted with ethyl acetate (3×200 ml). The organic layers were combined and washed with two 200 ml portions of water and 200 ml of brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The solid was stirred in hexanes for 1.5 hours and filtered again to afford the title compound.

後処理

  1. temperatureThe reaction mixture was heated to 60° C. for 1.5 h
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate (3×200 ml)
  4. washwashed with two 200 ml portions of water and 200 ml of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationfiltered again

出典と根拠

ORDレコード
ord-320ca4f908cc474bae0d74b4ba3de81e
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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