4-Methylmorpholine → N-Boc-(2S,3S)-(-)-2-Amino-3-methyl-1-pentanol

HRID 427382

Reaktionsgleichung

Reaktionsgleichung von HRID 427382
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7](O)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].CN1CCOCC1.ClC(OCC(C)C)=O>COCCOC>[C:10]([NH:1][C@H:2]([CH2:7][OH:8])[C@H:3]([CH2:5][CH3:6])[CH3:4])([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11]

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 2724762tert-Butoxycarbonyl-L-isoleucine

Produkt 1

HCID 14237729N-Boc-(2S,3S)-(-)-2-Amino-3-methyl-1-pentanolAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

In 5 ml of 1,2-dimethoxyethane (DME), 1.201 g of Boc-Ile-OH.1/2H2O was dissolved and 550 μl of N-methylmorpholine and 650 μl of isobutyl chloroformate were successively added dropwise at −15° C. After stirring for 1 min, the formed N-methylmorpholine hydrochloride was filtered off and washed twice with 2.5 ml each of DME. The filtrate and washings were combined and 284 mg of sodium borohydride in 2.5 ml of water was added in one portion. After 30 sec, 125 ml of water was added and the mixture was extracted with 25 ml of ethyl acetate and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure to give 1.040 g of the title compound.

Aufarbeitung

  1. dissolution1/2H2O was dissolved
  2. filtrationthe formed N-methylmorpholine hydrochloride was filtered off
  3. washwashed twice with 2.5 ml each of DME
  4. addition284 mg of sodium borohydride in 2.5 ml of water was added in one portion
  5. waitAfter 30 sec
  6. addition125 ml of water was added
  7. extractionthe mixture was extracted with 25 ml of ethyl acetate
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe dried solution was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-72b98dec643b46d8ac77cd6fa3033ca8
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313094B1

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