Benzaldehyde → HCID 20605629, compound

HRID 497421Notes

Reaction equation

HRID 497421 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:13]3[N:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][NH:10][CH2:9][C:8]=2[NH:7][CH:6]=1)=[O:4].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:13]3[N:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH2:11][N:10]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:9][C:8]=2[NH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 20605628HCID 20605628, compound

Product 1

HCID 20605629HCID 20605629, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 130 mg (0.53 mmol) of 3,4,5,6-Tetrahydro-3,5,10-triaza-benzo[e]azulene-1-carboxylic acid methyl ester and 0.6 mL (0.6 mmol of benzaldehyde is dissolved in 10 mL of dichloroethane. To this solution is added 270 mg (1.3 mmol) of sodium triacetoxyborohydride and the resulting mixture is stirred for 18 hours at room temperature. A 10 mL solution of saturated Na2HCO3 is added, and the reaction stirred for 60 minutes. The organic layer is separated from the aqueous layer, dried (Na2SO4) and evaporated. The residue is chromatographed on 10 grams of silica gel using 50/1 chloroform/methanol as the eluant. Appropriate fractions are combined to yield 118 mg of 5-benzyl-3,4,5,6-tetrahydro-3,5,10-triaza-benzo[e]azulene-1-carboxylic acid methyl ester. 1H NMR (CDCl3) δ 10.1 (s, 1H), 8.6 (d, 1H), 7.55 (d, 1H), 7.3 (m, 6H), 7.1 (m, 1H), 3.70 (s, 3H), 3.60 (s, 2H), 3.55 (s, 2H), 3.35 (s, 2H). Mass spectrum: m/e=334.3 (p+1). TLC (10/1 chloroform/methanol) Rf=0.15. Step 2 (Step 5′ in Scheme 11):

Workup

  1. stirringthe reaction stirred for 60 minutes
  2. customThe organic layer is separated from the aqueous layer
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue is chromatographed on 10 grams of silica gel using 50/1 chloroform/methanol as the eluant

Sources & evidence

ORD record
ord-fd2dd18ec42741da90c91f846c101648
Source dataset
uspto-grants-2005_09
Patent number
US06949562B2

Reaction notes

Loading…