Triphenylphosphine → HCID 131723727, compound

HRID 1633798Notes

Reaction equation

HRID 1633798 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-9da6ac1e88f84c118354d1d76286d07e
Source dataset
uspto-grants-2003_01
Patent number
US06504034B2

Reaction notes

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