2,4-Dichlorobenzaldehyde → (S)-tert-Butyl 3-((2,4-dichlorobenzyl)amino)pyrrolidine-1-carboxylate

HRID 252084

反応式

HRID 252084 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH:17]=O.[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13][CH2:17][C:16]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:15]=2[Cl:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 134042,4-DichlorobenzaldehydeHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 4311764Sodium borohydride

生成物 1

HCID 66854615(S)-tert-Butyl 3-((2,4-dichlorobenzyl)amino)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Stir a mixture of (S)-3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester (15.07 g, 81.0 mmol) and 2,4-dichlorobenzaldehyde (13.46 g, 76.9 mmol) in dry methanol (250 mL) at room temperature under nitrogen overnight. Add slowly sodium borohydride (4.74 g, 125.4 mmol) and stir for 10 min. Concentrate and add 2 N NaOH (150 mL) and extract with diethyl ether. Combine the organic layers, wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give (S)-3-(2,4-dichlorobenzylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester which may be used without further purification (26.9 g, 100%).

後処理

  1. stirringstir for 10 min
  2. concentrationConcentrate
  3. additionadd 2 N NaOH (150 mL)
  4. extractionextract with diethyl ether
  5. washwash with saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

出典と根拠

ORDレコード
ord-4d67d823c64943d4a40ecc1545da463a
出典データセット
uspto-grants-2011_01
特許番号
US07868014B2

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