Lithium borohydride → 3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester

HRID 446955Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH:9]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH2:8][CH2:7][N:6]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O.[Li+].[BH4-]>C1COCC1.CO>[C:21]([O:20][C:18]([N:6]1[CH2:7][CH2:8][CH:9]([O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]1[CH2:3][OH:2])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution containing 3-(tert-Butyldimethylsilanyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (3, 12 g, 33 mmol) in THF (50 mL) was cooled to 0° C. LiBH4 in THF (2M, 20 mL) was added in a dropwise fashion. After 1 h, the solution was warmed to ambient temperature. After 2 h, the solution was diluted with MeOH, then H2O, and concentrated. The residue was extracted with EtOAc, washed with 1M HCl, saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 9.5 g (87%) of 3-(tert-Butyldimethylsilanyloxy)-2-hydroxymethylpyrrolidine-1-carboxylic acid tert-butyl ester (4) as a colorless oil (See: Herdeis, C.; Hubmann, H. P.; Lotter, H. Tetrahedron: Asymmetry, 1994, 5, 119).

Workup

temperaturethe solution was warmed to ambient temperature
waitAfter 2 h
concentrationH2O, and concentrated
extractionThe residue was extracted with EtOAc
washwashed with 1M HCl, saturated aqueous NaHCO3, brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-1069663c25134a03ae523dbcf3d6d614
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481495B2

Reaction notes

Loading…