Triphenylphosphine → HCID 131723727, compound

HRID 1861023Notes

Reaction equation

HRID 1861023 reaction equation
[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][C@@H:7]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8]1)([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.[C:46](O)(=[S:48])[CH3:47]>C1COCC1>[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][C@H:7]1[CH2:11][CH2:10][C@H:9]([O:12][C:46](=[S:48])[CH3:47])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54118351(1S,3R)-3-{[tert-Butyl(dimethyl)silyl]oxy}cyclopentan-1-olHCID 178418634HCID 178418634, compound

Product 1

HCID 131723727HCID 131723727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (±)-cis-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol (from Example 51 above) (2.6 g, 12.02 mmol) and triphenyl phosphine (Aldrich, 7.9 g, 30.12 mmol) in dry THF (100 mL) at 0° C. was added dropwise diethyl azodicarboxylate (Aldrich, 4.8 mL, 30.48 mmol). After stirring for 15 minutes thioacetic acid (Aldrich, 2.2 mL, 30.78 mmol) was added dropwise. The reaction mixture was allowed to reach room temperature slowly and stirred overnight. Then, the reaction mixture was concentrated and the residue was purified by flash chromatography (silica gel, 0-5% ether in hexanes gradient) to give (±)-trans-thioacetic acid-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]ester as a light yellow liquid. (Yield 2.36 g, 72%).

Workup

  1. additionwas added dropwise
  2. customto reach room temperature
  3. concentrationThen, the reaction mixture was concentrated
  4. customthe residue was purified by flash chromatography (silica gel, 0-5% ether in hexanes gradient)

Sources & evidence

ORD record
ord-99dcebe02ab44b48917479b7f73ca8fd
Source dataset
uspto-grants-2003_03
Patent number
US06531598B1

Reaction notes

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