Triethylamine → HCID 20825661, 화합물

HRID 480001

반응식

HRID 480001 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].C(N(CC)CC)C.[CH3:20][N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[CH2:26][OH:27]>C1COCC1.CN(C1C=CN=CC=1)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:27][CH2:26][CH:22]1[CH2:23][CH2:24][CH2:25][N:21]1[CH3:20])=[O:8])([O-:3])=[O:2]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 643492(2S)-1-Methyl-2-pyrrolidinemethanol

생성물 1

HCID 20825661HCID 20825661, 화합물수율 78.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-nitrobenzoylchloride (2.5 g; 13.5 mmol) in THF (25 ml) was added triethylamine (1.87 ml; 13.5 mmol), a catalytic amount of 4-(N,N-dimethylamino)pyridine and (S)-(−)-1-methyl-2-pyrrolidinemethanol (1.61 ml; 13.5 mmol). The mixture was heated to reflux for 1.5 hours and left with stirring at ambient temperature overnight. The solvent was removed by evaporation and the residue was partitioned between dichloromethane and diluted hydrochloric acid (4 M). The aqueous phase was rendered alkaline by addition of aqueous sodium hydroxide (4 M) and extracted with dichloromethane. The organic extract was dried over sodium sulphate and evaporated to leave 6r (2.8 g; 78%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. waitleft
  4. customThe solvent was removed by evaporation
  5. customthe residue was partitioned between dichloromethane and diluted hydrochloric acid (4 M)
  6. additionby addition of aqueous sodium hydroxide (4 M)
  7. extractionextracted with dichloromethane
  8. extractionThe organic extract
  9. dry with materialwas dried over sodium sulphate
  10. customevaporated

출처 및 근거

ORD 기록
ord-25f4f7ebe0144f52b55f938f073b5169
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649609B2

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