Triphenylphosphine → HCID 86303716, compound

HRID 1484823Notes

Reaction equation

HRID 1484823 reaction equation
[C:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](O)[C:16]=1[CH:17]=[O:18].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[OH:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([O:13][CH2:12][C@@H:8]2[CH2:9][CH2:10][CH2:11][N:7]2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]=1[CH:17]=[O:18]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 102858012,6-DihydroxybenzaldehydeHCID 69850554HCID 69850554, compound

Product 1

HCID 86303716HCID 86303716, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-(1-phenylpyrrolidin-2-yl)methanol (45 mg, 0.23 mmol) and 2,6-dihydroxybenzaldehyde (60 mg, 0.46 mmol) in THF (1 ml) was added PPh3 (0.12 g, 0.46 mmol), followed by DIAD (90 mg, 0.46 mmol) at room temperature. After stirrer for 10 min, the mixture was concentrated and the residue was purified by column (Hexanes/EtOAc=9:1) to give (S)-2-hydroxy-6-((1-phenylpyrrolidin-2-yl)methoxy)benzaldehyde (14 mg). 1H NMR (400 MHz, CDCl3 (ppm) 11.96 (s, 1H), 10.37 (s, 1H), 7.35 (t, J=8.0 Hz, 1H), 7.25 (m, 2H), 6.73 (m, 3H), 6.53 (d, J=8.4 Hz, 1H), 6.33 (d, J=9.2 Hz, 1H), 4.21 (m, 1H), 4.15 (d, J=3.6 Hz, 1H), 3.83 (t, J=8.0 Hz, 1H), 3.53 (m, 1H), 3.22 (m, 1H), 2.11 (m, 4H); MS (ESI) m/z 298.4

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by column (Hexanes/EtOAc=9:1)

Sources & evidence

ORD record
ord-84e96378108041c39a81162ddc8950a5
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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