Formaldehyde → Dimethyl 13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate

HRID 421959Notes

Reaction equation

HRID 421959 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:29]([O:31][CH3:32])=[O:30])=[CH:12][C:13]=3[N:14]3[C:20]=2[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[NH:17][CH:16]([C:25]([O:27][CH3:28])=[O:26])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.O.[BH3-][C:37]#N.[Na+]>CO.CCN(CC)CC.CCOC(C)=O.CC(O)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:29]([O:31][CH3:32])=[O:30])=[CH:12][C:13]=3[N:14]3[C:20]=2[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]([CH3:37])[CH:16]([C:25]([O:27][CH3:28])=[O:26])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

9

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 66673930dimethyl 13-cyclohexyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate

Product 1

HCID 66674609Dimethyl 13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dimethyl 13-cyclohexyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate was dissolved in anhydrous MeOH (0.05M) and HOAc was added. the mixture was treated with a 37% solution of formaldehyde in water (1.2 eq.), then NaCNBH3 (1.2 eq.) was added. The solution was stirred for 2 h at RT. The product was isolated by flash chromatography (PE:EtOAc, 9:1, 0.5% NEt3). After evaporation of the solvents a colourless solid was obtained (quant.). (ES+) m/z 447 (M+H)+.

Workup

  1. customAfter evaporation of the solvents a colourless solid
  2. customwas obtained (quant.)

Sources & evidence

ORD record
ord-40eaae7400c54ce1a0540d9881934229
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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