Trifluoroacetic acid methylene chloride → 2-(4-Bromobenzyl)-8-(4-(SR)-phenylpyrrolidin-3-(RS)-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 1182162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182162
C(OC([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH2:19][N:20]2[CH2:38][CH2:37][C:23]3([C:27](=[O:28])[N:26]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=4)[CH2:25][CH2:24]3)[CH2:22][CH2:21]2)[CH2:9]1)=O)(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[Br:36][C:33]1[CH:32]=[CH:31][C:30]([CH2:29][N:26]2[CH2:25][CH2:24][C:23]3([CH2:22][CH2:21][N:20]([CH2:19][CH:10]4[CH:11]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)[CH2:12][NH:8][CH2:9]4)[CH2:38][CH2:37]3)[C:27]2=[O:28])=[CH:35][CH:34]=1

Komponenten

3

Edukt 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 673694643-(RS)-[2-(4-Bromobenzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-(SR)-phenylpyrrolidine-1-carboxylic Acid Tert-Butyl Ester

Produkt 1

HCID 673687102-(4-Bromobenzyl)-8-(4-(SR)-phenylpyrrolidin-3-(RS)-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-oneAusbeute 100,1 %

Versuchsvorschrift

To 510 mg (0.87 mmol) of 3-(RS)-[2-(4-bromobenzyl)-1-oxo-2,8-diaza-spiro[4.5]dec-8-ylmethyl]-4-(SR)-phenylpyrroli-dine-1-carboxylic acid tert-butyl ester was added a solution of DCM/TFA 20% (12 mL). The reaction mixture was agitated for one hour at room temperature before quenching with 30 mL of aqueous solution of sodium hydroxide (1N). The solution was then extracted with DCM (2×20 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated in vacuo yielding Compound 3 as a pale yellow solid (420 mg, 99.4%).

Aufarbeitung

  1. custombefore quenching with 30 mL of aqueous solution of sodium hydroxide (1N)
  2. extractionThe solution was then extracted with DCM (2×20 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bd8d522596704e75acd5a0b8e9877fd9
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288548B2

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