HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium borohydride → tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | Boc-L-phenylalanine methyl ester | HCID 9882138 | — |
| Reactant | Chloroform methanol | HCID 21584188 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate | HCID 2733675 | 89% |
Reaction Steps
This compound was prepared in 89% yield from the ester 4d (11.2 g, 40 mmol) by reduction with lithium borohydride in dry DME analogous to the method described earlier1,2. TLC Rf 0.50 (eluent MeOH/CHCl3, 7/93). 1H NMR (CDCl3) δ 1.40 (s, 9H, t-Bu), 2.00-2.53 (m, 1H, OH), 2,83 (d, J=5.4 Hz, 2H, CH2Ph), 3.33-4.08 (m, 3H, CH2OH, CHCH2), 4.48-4.94 (br d, 1H, NH), 7.22 (s, 5H, Ph). CI MS, m/e 252 (M+ +1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04820712 |
| Source dataset | uspto-grants-1989_04 |
| ORD ID | ord-86f75fe393ab42aea1de0f003f124fb6 |
| Source note | uspto-grants-1989_04 |