Sodium triacetoxyborohydride → HCID 69216108, compound

HRID 747838Notes

Reaction equation

HRID 747838 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:30][CH:15]([CH2:16][CH:17]([N:19]4[C:27](=[O:28])[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[C:20]4=[O:29])[CH2:18]2)[NH:14][CH2:13][CH:12]3[CH3:31])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].C(O[BH-](O[C:42](=O)[CH3:43])OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([C:11]23[CH2:30][CH:15]([CH2:16][CH:17]([N:19]4[C:20](=[O:29])[C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[C:27]4=[O:28])[CH2:18]2)[N:14]([CH2:2][CH2:1][CH2:3][C:42]2[CH:43]=[CH:9][CH:10]=[CH:5][CH:6]=2)[CH2:13][CH:12]3[CH3:31])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 69217200HCID 69217200, compound

Product 1

HCID 69216108HCID 69216108, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-[5-(3-Isopropoxy-phenyl)-4-methyl-2-aza-bicyclo[3.3.1]non-7-yl]-isoindole-1,3-dione (2.92 g, 7.0 mmol) and hydrocinamaldehyde (1.12 g, 8.3 mmol) were dissolved in dichloroethane (115 ml) followed by the addition of sodium triacetoxyborohydride (2.1 g, 9.7 mmol) and allowed to react at room temperature overnight. The reaction was quenched with the addition of a saturated sodium bicarbonate solution (200 ml) and the organic layer separated. The aqueous was then extracted with CHCl3. The combined organic fractions were dried (NaSO4), filtered, and concentrated in vaccu. The crude product was then purified by flash chromatography on an aluminum oxide (neutral, Brockman activity II-III) column and eluting with 8:2 hexane:ethyl acetate giving 3.16 g (83.9%) of the desired product. 1H NMR (CDCl3) δ 7.75 (m, 2H), 7.64 (m, 2H), 7.25 (m, 5H), 6.79 (m, 2H), 6.68 (d, J=7.8, 1H), 5.15 (m, 1H), 4.52 (sept., J=6.0 Hz, 1H), 3.27 (br, 1H), 3.08 (dd, J1=6 Hz, J2=3 Hz, 1H), 2.78-2.52 (m, 6H), 2.25-2.16 (m, 5H), 1.96-1.78 (m, 4H), 1.31 (d, J=6, 6H), 0.78 (d J=6.9, 3H).

Workup

  1. customto react at room temperature overnight
  2. customThe reaction was quenched with the addition of a saturated sodium bicarbonate solution (200 ml)
  3. customthe organic layer separated
  4. extractionThe aqueous was then extracted with CHCl3
  5. dry with materialThe combined organic fractions were dried (NaSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vaccu
  8. customThe crude product was then purified by flash chromatography on an aluminum oxide (neutral, Brockman activity II-III) column
  9. washeluting with 8:2 hexane

Sources & evidence

ORD record
ord-e91e2703108c43ca9ec90cd7980e38cc
Source dataset
uspto-grants-2008_07
Patent number
US07399762B2

Reaction notes

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