Triphenylphosphine → HCID 90408294, compound

HRID 1770793Notes

Reaction equation

HRID 1770793 reaction equation
[CH:1]([N:4]1[C:8]([C@@H:9]2[C@H:14]([CH2:15][OH:16])[CH2:13][CH2:12][O:11][CH2:10]2)=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].[OH:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22](O)[C:19]=1[CH:20]=[O:21].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:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22]([O:16][CH2:15][C@@H:14]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[C:8]2[N:4]([CH:1]([CH3:3])[CH3:2])[N:5]=[CH:6][CH:7]=2)[C:19]=1[CH:20]=[O:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 102858012,6-DihydroxybenzaldehydeHCID 90408693HCID 90408693, compound

Product 1

HCID 90408294HCID 90408294, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)((3S,4R)-3-(1-isopropyl-1H-pyrazol-5-yl)tetrahydro-2H-pyran-4-yl)methanol (50 mg, 0.22 mmol) and 2,6-dihydroxybenzaldehyde (60 mg, 0.44 mmol) in THF (1 mL) was added PPh3 (120 mg, 0.44 mmol) and DIAD (0.09 mL, 0.44 mmol) at 0° C. After stirred for 30 min, the solution was concentrated and the residue was purified by column (Hexanes/EtOAc=60:40) to give impure product, which was further purified by prep HPLC (eluted with ACN/H2O) to give (±) 2-hydroxy-6-(((3S,4R)-3-(1-isopropyl-1H-pyrazol-5-yl)tetrahydro-2H-pyran-4-yl)methoxy)benzaldehyde (6 mg). 1H NMR (400 MHz, CDCl3) (ppm) 11.90 (s, 1H), 10.36 (s, 1H), 7.79 (s, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.32 (t, J=8.8 Hz, 1H), 6.52 (d, J=8.4 Hz, 1H), 6.43 (d, J=1.6 Hz, 1H), 6.16 (d, J=8.0 Hz, 1H), 4.46 (m, 1H), 4.13 (dt, J=11.2, 4.0 Hz, 1H), 3.95 (dd, J=11.2, 3.2 Hz, 1H), 3.81 (dd, J=11.6, 3.2 Hz, 1H), 3.73 (dd, J=9.2, 5.6 Hz, 1H), 3.65 (dt, J=11.6, 3.2 Hz, 1H), 3.57 (t, J=8.8 Hz, 1H), 3.28 (d, J=4.0 Hz, 1H), 2.56 (m, 1H), 1.87 (m, 1H), 1.58 (m, 1H), 1.31 (d, J=6.8 Hz, 3H), 1.29 (d, J=7.6 Hz, 3H); MS (ESI) m/z 334.3 [M+H]+.

Workup

  1. concentrationthe solution was concentrated
  2. customthe residue was purified by column (Hexanes/EtOAc=60:40)
  3. customto give impure product, which
  4. customwas further purified by prep HPLC (eluted with ACN/H2O)

Sources & evidence

ORD record
ord-12043b2ec8214f01a7ca3f682b64aa48
Source dataset
uspto-grants-2016_02
Patent number
US09248199B2

Reaction notes

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