Triphenylphosphine → HCID 123288403, compound

HRID 708907Notes

Reaction equation

HRID 708907 reaction equation
[F:1][C:2]1[C:3]([OH:24])=[C:4]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[CH2:5][N:6]([CH3:17])[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Si:25]([O:32][CH2:33][C@H:34](O)[CH3:35])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].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>C1COCC1>[Si:25]([O:32][CH2:33][C@@H:34]([O:24][C:3]1[C:2]([F:1])=[CH:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][C:4]=1[CH2:5][N:6]([CH3:17])[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:35])([C:28]([CH3:29])([CH3:30])[CH3:31])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 13175135(2R)-1-{[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}propan-2-olHCID 117739360HCID 117739360, compound

Product 1

HCID 123288403HCID 123288403, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 27B (400 mg, 1.197 mmol), 33A (251 mg, 1.316 mmol) and triphenylphosphine (345 mg, 1.316 mmol) in THF (10 mL) at 0° C., was added DIAD (0.256 mL, 1.316 mmol) dropwise. The reaction mixture was allowed to slowly warm to rt and stirred for 16 h, then was concentrated. The crude product was purified by flash chromatography (0 to 40% ethyl acetate/hexanes) to give 33B (577 mg, 1.139 mmol, 95% yield) as colorless oil. MS (ESI) m/z: 507.1[M+1]+. 1H NMR (400 MHz, chloroform-d) δ ppm 7.78-7.94 (2H, m) 7.27-7.43 (5H, m) 5.17 (2H, d, J=20.1 Hz) 4.46-4.74 (3H, m) 3.65-3.81 (2H, m) 2.97 (3H, d, J=15.8 Hz) 1.31 (3H, t, J=7.0 Hz) 0.81 (9H, d, J=7.0 Hz) −0.05-0.04 (6H, m) rotamers.

Workup

  1. concentrationwas concentrated
  2. customThe crude product was purified by flash chromatography (0 to 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cf6f1c41faa84734bcfcb8a73053bfeb
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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