Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | rel-(3R,4R)-4-(Aminomethyl)-1-(phenylmethyl)-3-piperidinol | HCID 57986572 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68751819 | HCID 68751819 | 69% |
Reaction Steps
In a flask, was added (3S,4S)-4-(aminomethyl)-1-benzylpiperidin-3-ol (1.0 g, 4.5 mmol, Sunshine Labs), DMF (10 mL) and CDI (0.736 g, 4.54 mmol). The mixture was heated to about 65° C. for about 40 min. To the mixture was added EtOAc (20 mL) and washed with water (3×20 mL). The aqueous layers were combined and extracted with DCM (2×20 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated under vacuum to give (4aS,8aS)-7-benzyloctahydro-2H-pyrido[4,3-e][1,3]oxazin-2-one (0.773 g, 69%): LC/MS (Table 2, Method c) Rt=1.11 min.; MS m/z: 247 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08551981B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-c46d4a200ee840988354d45862bd1c8f |
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| Source note | uspto-grants-2013_10 |
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