Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Imidazole | HCID 795 | — |
| Reactant | tert-Butyldiphenylchlorosilane | HCID 94078 | — |
| Reactant | HCID 89585232 | HCID 89585232 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89585238 | HCID 89585238 | — |
| Product | HCID 90444768 | HCID 90444768 | — |
Reaction Steps
6.91 g (0.102 mol) of imidazole and 26.435 ml (0.201 mol) of tert-butyldiphenylchlorosilane were added successively at 22° C. to a solution of 19 g (0.058 mol) of tert-butyl (S)-3-(hydroxythiazol-2-yl-methyl)piperidine-1-carboxylate [diastereomer mixture] in 250 ml of dichloromethane. 250 ml of ice-water were added to the reaction mixture. The organic phase was dried over sodium sulfate, filtered and evaporated. The crude product was chromatographed over silica gel, giving 3.44 g of tert-butyl (S)-3-[(R)-(tert-butyldiphenylsilanyloxy)thiazol-2-ylmethyl]piperidine-1-carboxylate (rotation value in methanol [α]20D=+28.00) and 1.19 g of tert-butyl (S)-3-[(S)-(tert-butyldiphenylsilanyloxy)thiazol-2-ylmethyl]-piperidine-1-carboxylate (rotation value in methanol [α]20D=−1.3°); HPLC/MS (M+H)+=537.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09187469B2 |
|---|
| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-7b837307765245188f56ebec98264a82 |
|---|
| Source note | uspto-grants-2015_11 |
|---|
