HuagongsheHuagongshe Chemistry Print Report · For research reference only
benzyl (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(prop-1-en-2-yl)cyclohexylcarbamate → (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-isopropylcyclohexanamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | benzyl (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(prop-1-en-2-yl)cyclohexylcarbamate | HCID 86596867 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-isopropylcyclohexanamine | HCID 68766309 | 89.8% |
Reaction Steps
Benzyl (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(prop-1-en-2-yl)cyclohexylcarbamate (4.8 g) in MeOH (40 mL) was charged with 10% Pd/C, Degussa (600 mg). The reaction flask was evacuated and then back-filled with hydrogen; this was repeated three more times. The reaction was stirred under 1 atm of H2 for 4 h and then filtered and concentrated to provide (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-isopropylcyclohexanamine (2.9 g). MS (ES+)=272.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07482335B2 |
| Source dataset | uspto-grants-2009_01 |
| ORD ID | ord-f114afc605154f36b1df4ba43f98e301 |
| Source note | uspto-grants-2009_01 |