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

HRID 1243209Notes

Reaction equation

HRID 1243209 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

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23550265HCID 23550265, compound

Product 1

HCID 21062583(+)-(1S,3S)-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of (+)-(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol (745 mg, 3.44 mmol) (from Example 29b supra) and triphenyl phosphine (1.17 g, 4.47 mmol) (Aldrich) in anhydrous tetrahydrofuran (60 mL) was added dropwise diethyl azodicarboxylate (710 μL, 780 mg, 4.47 mmol) (Aldrich). After 2 to 3 minutes followed a dropwise addition of diphenylphosphoryl azide (950 μL, 1.23 g, 4.47 mmol) (Aldrich). The mixture was allowed to warm up slowly to room temperature stirred overnight and then partitioned between ethyl acetate and water. The organic layer was collected, dried over sodium sulfate, filtered, concentrated and the resulting residue was chromatographed on a silica gel column with a 0–20% diethyl ether in hexanes gradient to give (+)-(1S,3S)-(3-azido-cyclopentyloxy)-tert-butyl-dimethyl-silane as a colorless liquid. (Yield 589 mg, 70%).

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe resulting residue was chromatographed on a silica gel column with a 0–20% diethyl ether in hexanes gradient

Sources & evidence

ORD record
ord-cf3e0c704f744a99848a405b9552c807
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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