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Methyl iodide → tert-Butyl 4-{(3S)-4-[3-Methoxy-5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]-3-methylpiperazin-1-yl}-4-methylpiperidine-1-carboxylate

HRID 2244935
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2244935
[H-].[Na+].[OH:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=2)[CH:6]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3([CH3:36])[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)[CH2:19][CH:18]2[CH3:37])[CH2:5]1.[CH3:38]I>O1CCCC1>[CH3:38][O:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([F:16])([F:14])[F:15])[CH:11]=2)[CH:6]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3([CH3:36])[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]3)[CH2:19][C@@H:18]2[CH3:37])[CH2:5]1
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Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68741680tert-butyl 4-{4-[3-hydroxy-5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]-3-methylpiperazin-1-yl}-4-methylpiperidine-1-carboxylate

Produkt 1

HCID 86601777tert-Butyl 4-{(3S)-4-[3-Methoxy-5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]-3-methylpiperazin-1-yl}-4-methylpiperidine-1-carboxylateAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (150 mg, 3.75 mmol) in tetrahydrofuran (15 mL) was added a solution of tert-butyl 4-{4-[3-hydroxy-5-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]-3-methylpiperazin-1-yl}-4-methylpiperidine-1-carboxylate (92 mg, 0.185 mmol) in tetrahydrofuran (5 mL). The reaction mixture was stirred at room temperature for 1 h before methyl iodide (0.50 mL, 8.05 mmol) was added. The reaction was continuously stirred at room temperature overnight and quenched by addition of 10 mL of water and 10 mL of EtOAc. The organic phase was separated and the aqueous layer was extracted with EtOAc twice (2×15 mL). The combined extracts were washed with brine, dried over Na2SO4, and evaporated under reduced pressure to give the crude product (81 mg, 85%) which was used directly for the next step. LC-MS [M+1]=511.3.

Aufarbeitung

  1. additionwas added
  2. customquenched by addition of 10 mL of water and 10 mL of EtOAc
  3. customThe organic phase was separated
  4. extractionthe aqueous layer was extracted with EtOAc twice (2×15 mL)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ea806368d5db4bbd88ec6f66ddf80034
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07678798B2

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