(11S,11aS)-8-Methyl-7,9-dimethoxy-11-hydroxy-10-N-(2',2',2'-tri-chloroethoxylcarbonyl)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one → HCID 22046632, compound

HRID 1826152Notes

Reaction equation

HRID 1826152 reaction equation
[CH3:1][C:2]1[C:25]([O:26][CH3:27])=[CH:24][C:5]2[C:6](=[O:23])[N:7]3[CH2:22][CH2:21][CH2:20][C@H:8]3[C@H:9](O)[N:10](C(OCC(Cl)(Cl)Cl)=O)[C:4]=2[C:3]=1[O:28][CH3:29]>C1COCC1.CCOC(C)=O>[CH3:1][C:2]1[C:25]([O:26][CH3:27])=[CH:24][C:5]2[C:6](=[O:23])[N:7]3[CH2:22][CH2:21][CH2:20][CH:8]3[CH:9]=[N:10][C:4]=2[C:3]=1[O:28][CH3:29]

Participants

4

Reactant 1

HCID 23574476(11S,11aS)-8-Methyl-7,9-dimethoxy-11-hydroxy-10-N-(2',2',2'-tri-chloroethoxylcarbonyl)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

Product 1

HCID 22046632HCID 22046632, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Cd/Pb couple (1.34 g; 10.7 mmol Cd) was added to a rapidly stirring solution of 193 (1 g; 2.14 mmol) in a mixture of THF (15 ML) and 1 N NH4OAc (15 mL). After 3.5 hours the reaction was diluted with EtOAc (150 mL). The solution was dried over anhydrous MgSO4 and the solids were filtered and rinsed with EtOAc (50 mL). Removal of excess solvent yielded the product (194) as a white glass (554 mg, 2.021 mmol, 94%). 1H NMR (270 MHz, CDCl3) (mixture of imine and methyl ether forms) δ 7.72 (imine, d, J=4.39, 1H), 7.29 (s, 1H), 3.90 (s, 3H), 3.88-3.51 (m, 3H+2H+1H), 2.37-2.04 (m, 4H), 2.22 (s, 3H); 13C NMR (67.8 MHz, CDCl3) δ 164.65, 161.41, 156.79, 153.47, 133.87, 126.29, 124.27, 105.71, 60.98, 55.80, 55.70, 53.71, 46.70, 29.52, 29.34, 24.13, 9.33.

Workup

  1. dry with materialThe solution was dried over anhydrous MgSO4
  2. filtrationthe solids were filtered
  3. washrinsed with EtOAc (50 mL)
  4. customRemoval of excess solvent

Sources & evidence

ORD record
ord-20713516c3fe4c11a4038114d990c7f0
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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