HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → Dimethyl 13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | dimethyl 13-cyclohexyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate | HCID 66673930 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Dimethyl 13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate | HCID 66674609 | — |
Reaction Steps
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)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08101595B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-40eaae7400c54ce1a0540d9881934229 |
| Source note | uspto-grants-2012_01 |