Dichloromethane → HCID 44329050, compound

HRID 1421904Notes

Reaction equation

HRID 1421904 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 12327022(4aS,10bR)-1,2,3,4,4a,5,6,10b-Octahydrobenzo[f]quinolineHCID 217125654-(4-Phenylbenzoylamino)butyraldehyde

Product 1

HCID 44329050HCID 44329050, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (170 mg, 0.8 mmol) was added to a stirred mixture of cis-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinoline (D8b, 100 mg, 0.5 mmol), 4-(4-phenylbenzoylamino)butyraldehyde (143, 0.54 mmol) and acetic acid (1 drop) in 1,2-dichloroethane (8 ml) at room temperature. After stirring for 16 h, dichloromethane (10 ml) was added and the mixture was then washed with saturated aqueous K2CO3 (2×20 ml) and brine (20 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 gum (150 mg, 68%). Mass spectrum: found M+ 438.2679; C30H34N2O requires 438.2671.

Workup

  1. washthe mixture was then washed with saturated aqueous K2CO3 (2×20 ml) and brine (20 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-9559948ef733443e950c3f048d0f8837
Source dataset
uspto-grants-2000_06
Patent number
US06080752

Reaction notes

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