Cyclopentanol → HCID 67266974, compound

HRID 602501Notes

Reaction equation

HRID 602501 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:26]([O:28][C:29](=[O:41])[NH:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][C:32]=1O)[CH3:27].CCOC(/N=N/C(OCC)=O)=O>>[CH2:26]([O:28][C:29](=[O:41])[NH:30][C:31]1[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][C:36]=1[O:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:27]

Participants

5

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 15354720HCID 15354720, compound

Product 1

HCID 67266974HCID 67266974, compound

Procedure

Cyclopentanol (7.24 mL, 376 mM in dry tetrahydrofuran) was added to triphenylphosphine (1.44 g, polystyrene bound, 1.89 mMol/g) under argon, followed by the addition of a solution of (2-Hydroxy-4-nitrophenyl)-carbamic acid ethyl ester (25.6 mL, 62 mM in dry tetrahydrofuran) and a solution of diethylazodicarboxylate (7.24 mL, 376 mM in dry tetrahydrofuran). The reaction mixture was shaken at room temperature over night. The resin was filtered and washed with tetrahydrofuran (THF) (35 mL) and methanol (35 mL). The combined organic phase was evaporated in vacuo. The crude product was purified by flash chromatography (silica gel, heptane/ethyl acetate, gradient) to yield the title compound as slightly yellow solid (294 mg, 64%).

Workup

  1. filtrationThe resin was filtered
  2. washwashed with tetrahydrofuran (THF) (35 mL) and methanol (35 mL)
  3. customThe combined organic phase was evaporated in vacuo
  4. customThe crude product was purified by flash chromatography (silica gel, heptane/ethyl acetate, gradient)

Sources & evidence

ORD record
ord-f94d40e15391486a93a6fdce7823fd51
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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