Acetic Acid → HCID 14744532, compound

HRID 2259281Notes

Reaction equation

HRID 2259281 reaction equation
[CH2:1]([O:3][C:4]1([O:11][CH2:12][CH3:13])[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)[CH3:2].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[OH-].[Na+]>ClCCCl>[CH2:1]([O:3][C:4]1([O:11][CH2:12][CH3:13])[CH2:9][CH2:8][CH:7]([NH:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:6][CH2:5]1)[CH3:2]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 14744528HCID 14744528, compound

Product 1

HCID 14744532HCID 14744532, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

This compound is obtained according to the process described in Tet. Lett. 5595-5598, 1990. To 270 mmol of 4,4-diethoxycyclohexanone in 700 ml of stirred anhydrous 1,2-dichloroethane, at room temperature and under a nitrogen atmosphere, are added 270 mmol of benzylamine in 50 ml of 1,2-dichloroethane, 270 mmol of acetic acid and then 80 g of sodium triacetoxyborohydride. After stirring for 3 hours, 11 of saturated sodium hydrogen carbonate solution is poured onto the reaction medium. The pH is brought to 8 using 1N sodium hydroxide. The organic phase is recovered, dried and evaporated. The expected product is then obtained after purification of the residual oil by chromatography on a column of silica, using a dichloromethane/methanol/aqueous ammonia (95/5/0.5) mixture as eluent.

Workup

  1. customThis compound is obtained
  2. customThe organic phase is recovered
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-754925af135941bda062e5476ff33636
Source dataset
uspto-grants-1995_12
Patent number
US05472979

Reaction notes

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