Triphenylphosphine → HCID 15485233, compound

HRID 1872748Notes

Reaction equation

HRID 1872748 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:50][C:51]1([C:57]2[S:58][CH:59]=[CH:60][C:61]=2[O:62][CH3:63])[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][N:54]1[CH2:55][CH2:56][C:51]([OH:50])([C:57]2[S:58][CH:59]=[CH:60][C:61]=2[O:62][CH3:63])[CH2:52][CH2:53]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamateHCID 15485236HCID 15485236, compound

Product 1

HCID 15485233HCID 15485233, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.513 g (10 mmol) of (S)-(-)-2-(t-Butoxycarbonylamino)-3-phenyl-1-propanol was added at once to a magnetically stirred solution of 2.885 g (11 mmol) triphenylphosphine in tetrahydrofuran (100 mL) at 0° C. Thereafter 1.9 mL (12 mmol) diethyl azodicarboxylate was added dropwise over 3 minutes while the temperature was maintained between 0 and 5° C. This was immediately followed by adding a solution of 2.14 g (10 mmol) of 4-hydroxy-4-(3-methoxy-thiophen-2-yl)-piperidine in 100 mL tetrahydrofuran. The reaction mixture was stirred at ambient temperature overnight, evaporated in vacuo to dryness and the residue flash chromatographed on 300 g silica gel using chloroform as eluant yielding 2.6 g of the title compound as a faintly yellow dense oil.

Workup

  1. temperaturewas maintained between 0 and 5° C
  2. customevaporated in vacuo to dryness
  3. customthe residue flash chromatographed on 300 g silica gel

Sources & evidence

ORD record
ord-7cf677442f674ebe92bc1d53bddac99a
Source dataset
uspto-grants-2000_08
Patent number
US06110943

Reaction notes

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