HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → (+)-2-Chloro-n-[{1-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)(methyl)amino]cyclopentyl}(phenyl)methyl]-3-(trifluoromethyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-((Tert-butyldimethylsilyl)oxy)acetaldehyde | HCID 4187788 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | (+/-)-2-Chloro-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide | HCID 59347824 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (+)-2-Chloro-n-[{1-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)(methyl)amino]cyclopentyl}(phenyl)methyl]-3-(trifluoromethyl)benzamide | HCID 59347865 | 99.9% |
Reaction Steps
The title compound (0.390 g, 99%) was prepared from (±)-2-chloro-N-[[1-(methylamino)cyclopentyl](phenyl)methyl]-3-(trifluoromethyl)benzamide (0.282 g; 0.686 mmol), (tert-butyldimethylsilyloxy acetaldehyde (90%; 0.265 g; 1.52 mmol) and sodium triacetoxyborohydride (0.290 g; 1.52 mmol) in DCM (5 ml) in a similar manner to that described in E30. Mass Spectrum (Electrospray LC/MS). Found 569 (MH+). C29H4035ClF3N2O2Si requires 568. Ret. time: 3.04 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07745642B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-1b6c266b36d24e5ea66f57aad432bce0 |
| Source note | uspto-grants-2010_06 |