Triphenylphosphine → HCID 10707397, compound

HRID 2185406Notes

Reaction equation

HRID 2185406 reaction equation
N(C(OCC)=O)=N[C:3](OCC)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][O:33][C:34](=[O:48])[C@@H:35]1[CH2:39][C@@H:38]([OH:40])[CH2:37][N:36]1[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>O1CCCC1.C(O)=O>[CH3:32][O:33][C:34](=[O:48])[C@@H:35]1[CH2:39][C@H:38]([O:40][CH:3]=[O:4])[CH2:37][N:36]1[C:41]([O:43][C:44]([CH3:45])([CH3:47])[CH3:46])=[O:42]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 10707397HCID 10707397, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Diethyl azodicarboxylate (2.2 mL) was added to a cold (−15° C.) stirred solution of triphenyl phosphine (3.67 g) in tetrahydrofuran (40 mL). After stirring at 0° C. for 100 min, a solution of N-tert-butoxycarbonyl-trans-4-hydroxy-L-proline methyl ester (2.29 g) in tetrahydrofuran (20 mL) and formic acid (2.20 mL) were added. The mixture was stirred at room temperature for 14 hr, the solvent was removed and coevaporated several times with toluene in vacuo. The residue was diluted with toluene and precipitated solids were removed by filtration which was washed with toluene. The combined organic layers were evaporated in vacuo and the residue was purified by silica gel column chromatography (chloroform then chloroform:methanol=15:1, v/v) to give the title compound (4.07 g) as a pale yellow oil: 1H NMR (400 MHz, CDCl3) δ 1.39-1.50 (m, 9H), 2.25-2.34 (m, 1H), 2.43-2.60 (m, 1H), 3.54-3.67 (m, 1H), 3.72-3.83 (m, 1H), 3.75 (s, 3H), 4.37-4.55 (m, 1H), 5.35-4.41 (m, 1H), and 7.97 (s, 1H).

Workup

  1. stirringThe mixture was stirred at room temperature for 14 hr
  2. customthe solvent was removed
  3. additionThe residue was diluted with toluene
  4. customprecipitated solids
  5. customwere removed by filtration which
  6. washwas washed with toluene
  7. customThe combined organic layers were evaporated in vacuo
  8. customthe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-937ed81178fb49909bd20205445094db
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…