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

HRID 385779노트

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HRID 385779 반응식
[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

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 14923Ammonium HydroxideHCID 94429TriphosgeneHCID 22020939HCID 22020939, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-320ca4f908cc474bae0d74b4ba3de81e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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