Triphenylphosphine → HCID 23519861, compound

HRID 458319Notes

Reaction equation

HRID 458319 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][C@@H:8]([S:10][C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[S:30]([C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)(=[O:32])=[O:31])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O.CCOC(C)=O>[CH:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:41]=[CH:42][C:33]=1[S:30]([N:6]1[CH2:7][C@H:8]([S:10][C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:9][C@H:5]1[CH2:4][NH2:1])(=[O:32])=[O:31]

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 86584838HCID 86584838, compound

Product 1

HCID 23519861HCID 23519861, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.7 g (2.9 mmol) (2S,4R)-2-Azidomethyl-1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine were treated with 2.3 g (8.8 mmol, 3 eq) of triphenyl phosphine in 12 ml THF and 0.5 ml H2O for 2 days at RT. The solution was diluted with EtOAc, extracted with H2O and aqueous saturated NaHCO3 solution, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography on silica gel with CH2Cl2/MeOH 95:5 yielded 1.6 g (99%) (2S,4R)-C-[1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidin-2-yl]-methylamine as white foam, MS: 565 (MH+).

Workup

  1. extractionextracted with H2O and aqueous saturated NaHCO3 solution
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel with CH2Cl2/MeOH 95:5

Sources & evidence

ORD record
ord-e1e2a54364054a80a261b5374f41e39a
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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