Potassium Sodium Tartrate → HCID 18507140, compound

HRID 1355576Notes

Reaction equation

HRID 1355576 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)([CH2:11][CH2:12][CH2:13]Cl)[C:9]#[N:10])=[N:6][CH:7]=1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[CH2:11][CH2:12][CH2:13][NH:10][CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 18507150HCID 18507150, compound

Product 1

HCID 18507140HCID 18507140, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(5-bromo-pyridin-2-yl)-5-chloro-2-(3-methoxy-phenyl)-pentanenitrile (0.54 9, 1.43 mmol) in CH2Cl2 (3 mL) at -78oC was added DIBAL in CH2Cl2 (1M, 3.2 mL). The reaction mixture was stirred at -78 for 1 h and at room temperature for 4 h. The solution was poured to a saturated aqueous solution of Rochelle's salt (10 mL) and the resulting mixture was stirred vigorously for 16 h. The aqueous layer was washed with CH2Cl2 (3×10 mL), and the combined extracts were dried over Na2SO4 and concentrated. Purification by flash chromatography with CH2Cl2/MeOH (10:1) yielded 0.36 g of 5-bromo-3′-(3-methoxy-phenyl)-1′,2′,3′,4′,5′,6′-hexahydro-[2,3′]bipyridinyl. 1HNMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 7.63 (dd, 1H), 7.24-7.18(m, 1H), 6.91 (d, 1H) 6.81-6.67 (comp, 3H), 3.96-3.90 (m, 1H), 3.75 (s, 3H), 3.09-3.00 (comp, 2H), 2.82-2.74 (m, 1H), 2.54-2.48 (m, 1H), 2.41-2.34 (m, 1H) 1.64-1.60 (m, 1H) 1.38-1.31 (m, 1H); MS(M+1) 347.1, 349.1.

Workup

  1. stirringthe resulting mixture was stirred vigorously for 16 h
  2. washThe aqueous layer was washed with CH2Cl2 (3×10 mL)
  3. dry with materialthe combined extracts were dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography with CH2Cl2/MeOH (10:1)

Sources & evidence

ORD record
ord-372ad21fa122433dbb8ff60b19782f5a
Source dataset
uspto-grants-2003_07
Patent number
US06586431B1

Reaction notes

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