Acetonitrile → (3S*,4R*)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(isobutylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158493Notes

Reaction equation

HRID 1158493 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH:13]=O)[C@H:10]([C:15]([CH3:23])([CH3:22])[O:16][SiH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([NH2:28])[CH:25]([CH3:27])[CH3:26].CC#N.O.CC#N>O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:28][CH2:24][CH:25]([CH3:27])[CH3:26])[C@H:10]([C:15]([CH3:22])([CH3:23])[O:16][SiH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6558IsobutylamineHCID 18373917Acetonitrile--water (1/1)2×HCID 131728359(3S*,4S*)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131728367(3S*,4R*)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(isobutylamino-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound is prepared as described above for Example 9/step F (Scheme 5) from (3S*,4S*)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester and isobutylamine. MS (LC-MS): 401.1 [M+H]+; tR (HPLC, Waters Symmetry C18 column, 20-95% CH3CN/H2O/3.5 min, 95% CH3CN/H2O, 2 min, CH3CN and H2O containing 0.1% TFA, flow: 0.6 mL/min): 3.70 min.

Workup

  1. custom3.70 min.

Sources & evidence

ORD record
ord-a939507e9f1b4e889386b79da8c1f495
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

Loading…