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

HRID 252084

Reaktionsgleichung

Reaktionsgleichung von HRID 252084
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4d67d823c64943d4a40ecc1545da463a
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868014B2

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