HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → tert-butyl N-((2R)-3-hydroxy-2-methylpropyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethyl Sulfide | HCID 1068 | — |
| Reactant | Borane;tetrahydrofuran | HCID 2723981 | — |
| Reactant | (R)-3-((tert-butoxycarbonyl)amino)-2-methylpropanoic acid | HCID 11041840 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-butyl N-((2R)-3-hydroxy-2-methylpropyl)carbamate | HCID 10655267 | 61% |
Reaction Steps
To a 0° C. mixture of (2R)-3-t-butoxycarbonylamino-2-methylpropionic acid (4.6 g, 21.0 mmol) in THF (100 mL) was added 2 M Me2S.BH3/THF (16 mL, 31.5 mmol, 1.5 equivalents). After stirring for 2 h, water was added and the mixture stirred for 18 h. The mixture was diluted with CH2Cl2 and washed with satd Na2CO3. The organic layer was dried (Na2SO4), concentrated, and chromatographed (CH2Cl2; EtOAc) to give the title compound as an oil (2.4 g, 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07615568B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-2b494a6a528a473cad84ab2bf30c465c |
| Source note | uspto-grants-2009_11 |