Triethylamine → Carbonic acid 1,8-bis-dimethylamino-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester

HRID 44136노트

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HRID 44136 반응식
[CH3:1][N:2]([CH3:27])[N:3]1[C:7]2([CH2:12][CH2:11][N:10]([N:13]([CH3:15])[CH3:14])[CH2:9][CH2:8]2)[C:6](=[O:16])[CH:5]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[C:4]1=[O:26].C(N(CC)CC)C.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37]>O1CCCC1>[CH2:39]([O:38][C:36](=[O:37])[O:16][C:6]1[C:7]2([CH2:12][CH2:11][N:10]([N:13]([CH3:14])[CH3:15])[CH2:9][CH2:8]2)[N:3]([N:2]([CH3:1])[CH3:27])[C:4](=[O:26])[C:5]=1[C:17]1[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=1[CH3:25])[CH3:40]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 682286451,8-Bis-dimethylamino-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione

생성물 1

HCID 68228258Carbonic acid 1,8-bis-dimethylamino-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

150 mg 1,8-Bis-dimethylamino-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]decane-2,4-dione (PREPARATION EXAMPLE 1) is dissolved in 3 ml tetrahydrofuran, 75 mg triethylamine is added, and the mixture is cooled to 0° C. 44 mg ethyl chloroformate is added and the resulting suspension stirred for 3 hours, thereby warming to room temperature. Then the mixture is partitioned between water and ethyl acetate, the organic layer separated and washed with brine, dried over anhydrous sodium sulfate, and evaporated. The residue is purified by chromatography on silica gel with ethyl acetate/heptane (1:1) as a solvent. Thus, 145 mg Carbonic acid 1,8-bis-dimethylamino-2-oxo-3-(2,4,6-trimethyl-phenyl)-1,8-diaza-spiro[4.5]dec-3-en-4-yl ester ethyl ester is obtained as a solid, mp 105° C. 1H-NMR (CDCl3): 6.83 ppm (s, 2H), 4.02 ppm (q, 2H), 3.05 ppm (m, 2H), 2.94 ppm (s, 6H), 2.80 ppm (m, 2H), 2.43 ppm (s, 6H), 2.40 ppm (m, 2H), 2.23 ppm (s, 3H), 2.17 ppm (s, 6H), 1.86 ppm (m, 2H), 1.08 ppm (t, 3H).

후처리

  1. temperaturewarming to room temperature
  2. customThen the mixture is partitioned between water and ethyl acetate
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue is purified by chromatography on silica gel with ethyl acetate/heptane (1:1) as a solvent

출처 및 근거

ORD 기록
ord-42a0a72d026b4f8f8fc5d557b54924f3
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541343B2

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