HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium borohydride → tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | N-(tert-Butoxycarbonyl)-L-valine methyl ester | HCID 11031717 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate | HCID 7021464 | 81% |
Reaction Steps
This compound was prepared in 81% yield from the ester 4b (9.28 g, 40 mmol) by reduction with lithium borohydride in dry DME following the procedure that has been described earlier1,2. TLC Rf 0.47 (eluent MeOH/CHCl3,7/93). 1H NMR (CDCl3) δ 0.91 and 0.98 (dd, J=2 Hz, 6H, CH3CHCH3), 1.44 (s, 9H, t-Bu), 1.45-1.97 (m, 1H, CH3CHCH3), 2.15 (s, 1H, OH), 3.24-3.49 (m, 1H, CHCH2), 3.53-3.72 (m, 2H, CH2OH), 4.36-4.77 (m, 1H, NH). CI MS, m/e 204 (M+ +1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04820712 |
| Source dataset | uspto-grants-1989_04 |
| ORD ID | ord-29c26da8a0be4c3a8095f527ddb78703 |
| Source note | uspto-grants-1989_04 |