Triethylamine → Tert-butyl 7-propionyl-2,7-diazaspiro[4.4]nonane-2-carboxylate

HRID 1959421노트

반응식

HRID 1959421 반응식
[CH2:1]1[C:5]2([CH2:9][CH2:8][NH:7][CH2:6]2)[CH2:4][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:2]1.CCN(CC)CC.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>C(Cl)Cl>[C:24]([N:7]1[CH2:6][C:5]2([CH2:1][CH2:2][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]2)[CH2:9][CH2:8]1)(=[O:27])[CH2:25][CH3:26]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 23282813tert-Butyl 2,7-diazaspiro[4.4]nonane-2-carboxylate

생성물 1

HCID 66745092Tert-butyl 7-propionyl-2,7-diazaspiro[4.4]nonane-2-carboxylate수율 97.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a solution of tert-butyl 3,7-diazaspiro[4.4]nonane-3-carboxylate (127 mg, 0.56 mmol) in anhydrous DCM (1 mL), cooled in an ice water bath was added Et3N (57 mg, 78 μL, 0.56 mmol), followed by the addition of propanoyl chloride (57 mg, 54 μL, 0.62 mmol) as a solution in DCM (0.2 mL). The reaction mixture was stirred for 20 minutes, diluted with DCM and was washed with 1M HCl (×2) and brine (×1). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl 3-propanoyl-3,7-diazaspiro[4.4]nonane-7-carboxylate (154 mg, 97%) as an orange oil. 1H NMR (400 MHz, CDCl3) δ 3.73-3.11 (m, 8H), 2.34-2.17 (m, 2H), 1.97-1.70 (m, 4H), 1.46 (s, 9H), 1.16 (t, J=7.4 Hz, 3H). LC/MS m/z 283.5 [M+H]+.

후처리

  1. washwas washed with 1M HCl (×2) and brine (×1)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b97e9dcaae534d38b7fecec4fb617833
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410112B2

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