Triethylamine → HCID 20825661、化合物

HRID 480001

反応式

HRID 480001 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 20825661HCID 20825661、化合物収率 78.5%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-25f4f7ebe0144f52b55f938f073b5169
出典データセット
uspto-grants-2003_11
特許番号
US06649609B2

関連ノート

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