Triphenylphosphine → HCID 67235237, compound

HRID 1748309Notes

Reaction equation

HRID 1748309 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:41]=2)[CH:36]=[C:35]1[C:48]([O:50][CH2:51][CH3:52])=[O:49].[C:53]([O:57][C:58]([NH:60][CH2:61][C:62]1([CH2:75]O)[CH2:67][CH2:66][N:65]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[CH2:64][CH2:63]1)=[O:59])([CH3:56])([CH3:55])[CH3:54]>C1COCC1>[C:71]([O:70][C:68]([N:65]1[CH2:66][CH2:67][C:62]([CH2:75][N:34]2[C:42]3[C:37](=[CH:38][CH:39]=[C:40]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH:41]=3)[CH:36]=[C:35]2[C:48]([O:50][CH2:51][CH3:52])=[O:49])([CH2:61][NH:60][C:58]([O:57][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:59])[CH2:63][CH2:64]1)=[O:69])([CH3:73])([CH3:74])[CH3:72]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 44754779Diethyl 1H-indole-2,6-dicarboxylateHCID 67235084HCID 67235084, compound

Product 1

HCID 67235237HCID 67235237, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of triphenylphosphine (19.4 g, 74.1 mmol) and DIAD (14.05 mL, 74.1 mmol) in THF (700 mL) is cooled to 0° C. and stirred for 10 min. Diethyl 1H-indole-2,6-dicarboxylate (15.47 g, 59.3 mmol) is added and reaction mixture is stirred for another 10 min. tert-Butyl 4-{[(tert-butoxycarbonyl)amino]methyl}-4-(hydroxymethyl)piperidine-1-carboxylate (17 g, 49.4 mmol) is added and the reaction mixture is stirred for 48 h at room temperature. The mixture is partitioned between water and ethyl acetate. and the organic layer is separated. The aqueous layer is extracted with ethyl acetate (2×200 mL). The combined organic layers are dried (Na2SO4), and concentrated. The residue is purified by flash column chromatography using 15% EtOAc in petroleum ether to afford the title compound (17 g, 32%) as a dark brown oil.

Workup

  1. customreaction mixture
  2. additionis added
  3. stirringthe reaction mixture is stirred for 48 h at room temperature
  4. customThe mixture is partitioned between water and ethyl acetate
  5. customand the organic layer is separated
  6. extractionThe aqueous layer is extracted with ethyl acetate (2×200 mL)
  7. dry with materialThe combined organic layers are dried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-e03f872121fb4c5a846f1d02715a6ef4
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

Loading…