Tetrabutylammonium Fluoride → 2-(2-Benzyloxycarbonylamino-ethyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1965153Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][Si](C(C)(C)C)(C)C)[CH2:10][CH:9]1[CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH2:10][CH:9]1[CH2:21][CH2:22][NH:23][C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution containing 4 (5.9 g, 12.5 mmol) in anhydrous THF (100 mL) was cooled to 0° C. TBAF (1M/THF, 14 mL, 14.0 mmol) was added in one portion. After 5 h, the reaction mixture was diluted with EtOAc and washed successively with 1M HCl and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 to 1:3 hexanes/EtOAc) to afford 4.1 g (91%) of 5. 1H NMR (CDCl3, 300 MHz): δ7.31 (m, 5H), 5.93 (m, 1H), 5.07 (m, 2H), 4.37 (m, 1H), 4.03 (m, 1H) 3.51-3.06 (m, 4H), 2.05 (m, 1H), 1.77 (m, 1H), 1.44 (s, 9H) ppm. Mass spectrum, m/z [365.2] (M+H)+.

Workup

washwashed successively with 1M HCl and brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash silica gel chromatography (1:1 to 1:3 hexanes/EtOAc)

Sources & evidence

ORD record: ord-bfd391395e604ea4b58c95a895187d15
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415486B2

Reaction notes

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