Hydrochloric Acid → HCID 86756222, compound

HRID 565657Notes

Reaction equation

HRID 565657 reaction equation
[CH:1]([CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2([CH3:31])[CH2:15][C:14]3[C:16]([CH3:30])=[C:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:18]([CH3:21])=[C:19]([CH3:20])[C:13]=3[O:12]2)[CH2:6][CH2:5]1)=O.[C:32]1([CH:38]([NH2:45])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C([BH3-])#N.[Na+].CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2.Cl.C(=O)([O-])O.[Na+]>C(O)C>[C:32]1([CH:38]([NH:45][CH2:1][CH2:3][CH:4]2[CH2:5][CH2:6][N:7]([CH2:10][C:11]3([CH3:31])[CH2:15][C:14]4[C:16]([CH3:30])=[C:17]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[C:18]([CH3:21])=[C:19]([CH3:20])[C:13]=4[O:12]3)[CH2:8][CH2:9]2)[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6451Bromocresol GreenHCID 7036BenzhydrylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 53952919HCID 53952919, compound

Product 1

HCID 86756222HCID 86756222, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of tert-butyl [2-[[4-(formylmethyl)-1-piperidinyl]methyl]-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate (1.5 g) and 1,1-diphenylmethylamine (0.60 mL) in ethanol (20 mL) was stirred on an ice bath for 30 minutes. Then, 0.26 g of sodium cyanoborohydride and a small amount of bromocresol green were added. Thereafter, 4N-HCl solution in ethanol was added until the reaction mixture had turned yellow. The mixture was stirred for 1 hour, after which it was poured in an excess of aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate and the extract was washed with saturated aqueous NaCl and dried over MgSO4. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=4:1 to ethyl acetate) to provide 1.6 g of the title compound. Yield 77%.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=4:1 to ethyl acetate)

Sources & evidence

ORD record
ord-7565f0d39aff4308bd3925b0e093ab1b
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

Loading…