Dichloromethane → HCID 54162463, compound

HRID 1421903Notes

Reaction equation

HRID 1421903 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]1[C@@H:24]2[C@H:19]([CH2:20][CH2:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=32)[NH:18][CH2:17][CH2:16]1.[C:29]1([C:35]2[CH:48]=[CH:47][C:38]([C:39]([NH:41][CH2:42][CH2:43][CH2:44][CH:45]=O)=[O:40])=[CH:37][CH:36]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.ClCCl>C(O)(=O)C.ClCCCl>[C:29]1([C:35]2[CH:36]=[CH:37][C:38]([C:39]([NH:41][CH2:42][CH2:43][CH2:44][CH2:45][N:18]3[C@@H:19]4[C@H:24]([C:23]5[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=5[CH2:21][CH2:20]4)[CH2:15][CH2:16][CH2:17]3)=[O:40])=[CH:47][CH:48]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 11030553trans-1,2,3,4,4a,5,6,10b-Octahydro-benzo[f]quinolineHCID 217125654-(4-Phenylbenzoylamino)butyraldehyde

Product 1

HCID 54162463HCID 54162463, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (340 mg, 1.6 mmol) was added to a stirred mixture of trans-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline (D8a, 200 mg, 1 mmol), 4-(4-phenylbenzoylamino)butyraldehyde (286 mg, 01.1 mmol) and acetic acid (1 drop) in 1,2-dichloroethane (10 ml) at room temperature. After stirring for 16 h, dichloromethane (20 ml) was added and the mixture was then washed with saturated aqueous K2CO3 (2×25 ml) and brine (25 ml). Drying (Na2SO4) and evaporation in vacuo afforded an oil which was purified by preparative TLC on Kieselgel using 10% methanol-ethyl acetate as eluent to give the title compound as a colourless solid (200 mg, 46%).

Workup

  1. washthe mixture was then washed with saturated aqueous K2CO3 (2×25 ml) and brine (25 ml)
  2. customDrying
  3. custom(Na2SO4) and evaporation in vacuo
  4. customafforded an oil which
  5. customwas purified by preparative TLC on Kieselgel

Sources & evidence

ORD record
ord-8b11a750a55e4a8ea382687e9ded0e60
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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