Triphenylphosphine → (-)-(1R,3R)-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane

HRID 1243201Notes

Reaction equation

[C:1]([Si:5]([CH3:14])([CH3:13])[O:6][C@@H:7]1[CH2:11][CH2:10][C@H:9](O)[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.C1(P([N:60]=[N+:61]=[N-:62])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[N:60]([C@@H:9]1[CH2:10][CH2:11][C@@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:14])[CH3:13])[CH2:8]1)=[N+:61]=[N-:62]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of (−)-(1S,3R)-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol (670 mg, 3.09 mmol) (from Example 27b supra) and triphenyl phosphine (1.06 g, 4.02 mmol) (Aldrich) in anhydrous tetrahydrofuran (60 mL) cooled at 0° C. was added dropwise diethyl azodicarboxylate (640 μL, 0.70 g, 4.02 mmol) (Aldrich). After 2 to 3 minutes, followed a dropwise addition of diphenylphosphoryl azide (860 μL, 1.1 g, 4.02 mmol) (Aldrich). The mixture was allowed to slowly warm up to room temperature and after overnight stirring was partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate filtered and concentrated to a residue that was purified by chromatography with a silica gel column using a 0–20% diethyl ether in hexanes gradient to give (−)-(1R,3R)-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane as a colorless liquid. (Yield 540 mg, 72%).

Workup

temperatureto slowly warm up to room temperature and after overnight
customwas partitioned between ethyl acetate and water
customThe organic layer was collected
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated to a residue that
customwas purified by chromatography with a silica gel column

Sources & evidence

ORD record: ord-ad38a2ca41974da6a72d41295365d01e
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115740B2

Reaction notes

Loading…