HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → (2R,4S,5S)-2-benzhydryl-5-[(1H-indol-5-ylmethyl)-amino]-tetrahydro-pyran-4-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Indole-5-carboxaldehyde | HCID 589040 | — |
| Reactant | (2R,4S,5S)-5-amino-2-benzhydryl-tetrahydropyran-4-ol | HCID 11594377 | — |
| Reactant | (2S)-2-benzhydryl-3,6-dihydro-2H-pyran | HCID 54762285 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | (2R,4S,5S)-2-benzhydryl-5-[(1H-indol-5-ylmethyl)-amino]-tetrahydro-pyran-4-ol | HCID 11618477 | — |
Reaction Steps
(2R,4S,5S)-5-amino-2-benzhydryl-tetrahydropyran-4-ol 31b (0.05 g, 0.18 mmol) was reacted with 1H-indol-5-carbaldehyde (0.03 g, 0.18 mmol), glacial acetic acid (0.01 g, 0.18 mmol) and NaCNBH3 (0.02 g, 0.35 mmol) (Procedure C) to give (2R,4S,5S)-2-benzhydryl-5-[(1H-indol-5-ylmethyl)-amino]-tetrahydropyran-4-ol, (+)32b, 0.05 g (69%, [α]D=(+) 70.9, c=1, Acetone).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08519159B2 |
| Source dataset | uspto-grants-2013_08 |
| ORD ID | ord-c753c7d2bdfc45e0befb1221cd8660a4 |
| Source note | uspto-grants-2013_08 |