Furfuryl Alcohol → HCID 86592435, compound

HRID 273192Notes

Reaction equation

HRID 273192 reaction equation
[CH2:1]([O:8][N:9]([CH2:12][CH:13]1[CH:17]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][N:15]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[C:14]1=[O:30])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH2:36]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([O:8][N:9]([CH2:12][CH:13]1[CH:17]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][N:15]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:36][C:32]3[O:31][CH:35]=[CH:34][CH:33]=3)=[CH:25][CH:24]=2)[C:14]1=[O:30])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7361Furfuryl AlcoholHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86592434HCID 86592434, compound

Product 1

HCID 86592435HCID 86592435, compoundYield 318.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (+/−)-(3RS,4SR)-N-benzyloxy-N-[4-butyl-1-(4-hydroxybenzyl)-2-oxopyrrolidin-3-yl-methyl]formamide (0.1 g, 0.24 mmol) in tetrahydrofuran (3 mL) under argon was added furan-2-yl-methanol (0.041 mL, 0.048 mmol) and triphenylphosphine (0.07 g, 0.27 mmol). The solution was cooled to 0° C. and diethyl azodicarboxylate (0.042 mL, 0.27 mmol) was added dropwise. The reaction mixture was warmed up to rt and stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 (10 mL) and extracted with dichloromethane (3×10 mL). The combined extractions were dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 1:1) to afford (+/−)-(3RS,4SR)-N-benzyloxy-N-{4-butyl-1-[4-(furan-2-yl- methoxy)benzyl]-2-oxopyrrolidin-3-yl-methyl}formamide as a colorless oil (0.075 g, 63%). MS(ES) m/e 491 [M+H]+.

Workup

  1. temperatureThe reaction mixture was warmed up to rt
  2. customThe reaction was quenched with saturated aqueous NaHCO3 (10 mL)
  3. extractionextracted with dichloromethane (3×10 mL)
  4. extractionThe combined extractions
  5. dry with materialwere dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 1:1)

Sources & evidence

ORD record
ord-bae36bbc07084b6b99178214a2a420fb
Source dataset
uspto-grants-2008_11
Patent number
US07456211B2

Reaction notes

Loading…