Acetic Acid → methyl 14-cyclohexyl-7-[[2-(dimethylamino)ethyl](methyl)amino]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1714014Notes

Reaction equation

HRID 1714014 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([O:34][CH3:35])=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([NH:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[C:38](O)(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:32]([O:34][CH3:35])=[O:33])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]([N:26]([CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH3:38])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 68508425methyl 14-cyclohexyl-7-{[2-(dimethylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 68509901methyl 14-cyclohexyl-7-[[2-(dimethylamino)ethyl](methyl)amino]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 14-cyclohexyl-7-{[2-(dimethylamino)ethyl]amino}-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (prepared as described in Example 9, Step 5) in DCM (0.1 M), was added formaldehyde (3.0 eq) and acetic acid (5.5 eq), followed by sodium cyanoborohydride (3 eq). NaOH (20 eq, 1 N) was added after 2 h, and after stirring for 5 min the mixture was taken into EtOAc and washed with water and brine. Drying over sodium sulfate and concentration in vacuo gave the crude product, which was used without further purification; MS (ES+) m/z 490 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialDrying over sodium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-6d44d474a95a4d279f60d69831c4f5d5
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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