Triphenylphosphine → HCID 178454068, compound

HRID 656331Notes

Reaction equation

HRID 656331 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[N:16]1[CH:21]=[CH:20][C:19](O)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[N:16]1[CH:21]=[CH:20][C:19]([O:1][C@H:2]2[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178418642HCID 178418642, compoundHCID 178418813HCID 178418813, compound

Product 1

HCID 178454068HCID 178454068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., to a mixture of tert-butyl (cis-4-hydroxycyclohexyl)carbamate (100 mg, 0.5 mmol), 4-pyridinol (106 mg, 1.11 mmol), and triphenylphosphine (292 mg, 1.11 mmol) in tetrahydrofuran (2 mL) was added diethyl azodicarboxylate (176 μL, 1.11 mmol) with stirring. The mixture was stirred at r.t. overnight, then quenched with sat'd NH4Cl solution, and extracted with ethyl acetate. The extract was washed with water twice, brine once. Then, the extracdt was dried over Na2SO4. After filtration, the filtrate was concentrated to yield tert-butyl [trans-4-(pyridin-4-yloxy)cyclohexyl]carbamate.

Workup

  1. stirringThe mixture was stirred at r.t. overnight
  2. customquenched with sat'd NH4Cl solution
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water twice
  5. dry with materialThen, the extracdt was dried over Na2SO4
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2dfe7c8efb874890b4f53227a3160aff
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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