Diisopropylamine → (3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2099362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2099362
[N:1]1([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@@H:2]1[C:11]([OH:13])=O.Cl.[CH3:22][N:23](C)[OH:24].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCC[CH2:36]1.C(NC(C)C)(C)C>ClCCl.C(OCC)(=O)C>[CH3:36][O:24][N:23]([CH3:22])[C:11]([C@H:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][N:1]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:13]

Komponenten

7

Edukt 4

HCID 7912DiisopropylamineHCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 688607(3R)-2-[(tert-butoxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 2733179PyBroP

Produkt 1

HCID 86597541(3R)-tert-butyl 3-(methoxy(methyl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylateAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6.95 g of Boc-D-Tic-OH are dissolved in 25 ml of dichloromethane. 2.69 g of dimethylhydroxylamine hydrochloride and 11.68 g of bromotrispyrrolidino-phosphonium hexafluorophosphate are added. After cooling of the solution to 0° C., 9.72 ml of diisopropylamine are slowly added. The reaction medium is then stirred at ambient temperature for 16 h. After hydrolysis, extraction is carried out with ethyl acetate until the aqueous phase is completely depleted. Drying over MgSO4 and concentration to dryness are carried out. The crude obtained is chromatographed on silica gel, elution being carried out with a 99/1 mixture of dichloromethane and methanol. 7.4 g of tert-butyl (3R)-3-{[methoxy(methyl)amino]carbonyl}-3,4-dihydroisoquinoline-2(1H)-carboxylate are obtained.

Aufarbeitung

  1. customAfter hydrolysis, extraction
  2. dry with materialDrying over MgSO4 and concentration to dryness
  3. customThe crude obtained
  4. customis chromatographed on silica gel, elution
  5. additionbeing carried out with a 99/1 mixture of dichloromethane and methanol

Quellen und Nachweise

ORD-Eintrag
ord-0f9a7043712d4c6d9f1ed3657a2c4f6c
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569582B2

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