Pyridine → 3-Hydroxy-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

HRID 1965158Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][Si](C(C)(C)C)(C)C)[CH:10]2[N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:22][CH2:23][CH:9]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]2[N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:22][CH2:23][CH:9]12)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution containing 10 (868 mg, 1.8 mmol) in THF (10 mL) was cooled to 0° C. HF.pyridine reagent (1 mL, 36 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. After 16 h, the reaction mixture was diluted with EtOAc and washed successively with water, aqueous NaHCO3, water, and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc) to afford 600 mg (90%) of 11. 1H NMR (CDCl3, 300 MHz): δ7.29 (m, 5H), 5.10 (app dd, J=22.7, 12.5 Hz, 2H), 4.32 (m, 4H), 3.71 (m, 2H), 3.58 (m, 1H), 3.38 (m, 1H), 3.17 (m, 1H), 2.14 (m, 1H), 2.02 (m, 1H), 1.42 (s, 9H) ppm. Mass spectrum, m/z [363.2] (M+H)+.

Workup

temperatureto warm to ambient temperature
washwashed successively with water, aqueous NaHCO3, water, and brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record: ord-b7088a35d8b54d3b8c5f6da471b268e8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415486B2

Reaction notes

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