Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | HCID 67212430 | HCID 67212430 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | Formaldehyde | HCID 712 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Ammonia | HCID 222 | — |
| Product | HCID 67212526 | HCID 67212526 | 133.8% |
Reaction Steps
To a mixture of the above described 7-benzenesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane (1.25 g, 4.658 mmol) in acetonitrile (40 ml) and 36.5% formaldehyde solution in water (0.53 ml, 6.987 mmol) and 5 drops of acetic acid at 23° C. was added sodium cyanoborohydride (1.464 g, 23.29 mmol) and the mixture was stirred at 23° C. for 2 h. Poured onto water and extracted twice with ethyl acetate, dried the organic layer over sodium sulfate, filtered off, evaporated all volatiles totally and dried in high vacuum to give after silica gel column chromatography with ethyl acetate and additional methanol and aqueous ammonia solution the title compound as a colorless oil (0.88 g, 67%), MS (ISP) m/e=283.1 [(M+H)+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163740B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-51a9defc6b4140ebbd75bd3f1e939bd5 |
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| Source note | uspto-grants-2012_04 |
|---|