HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropylamine → (3S*,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropylamine | HCID 6363 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Reactant | (3S*,4S*)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 131728359 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (3S*,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-(isopropylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 131728361 | — |
Reaction Steps
The title compound is prepared in a similar manner as described for Example 9/reaction step F, from (3S*,4S*)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (19.3 g, 56.1 mmol), isopropylamine (14.5 mL, 168 mmol) and NaBH(OAc)3 (29.7 g, 140 mmol) in 1,2-dichloroethane (0.5 L) as a yellowish oil. MS: 387.2 [M+H]+. tR (HPLC, C18 column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 5.34 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807709B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-3d367221641f4725a02dc59658c7f250 |
| Source note | uspto-grants-2010_10 |