4-Chlorophenol → HCID 69669804, compound

HRID 1943589Notes

Reaction equation

HRID 1943589 reaction equation
[OH:1][CH:2]1[CH2:5][C:4]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:37][C:38]1[CH:43]=[CH:42][C:41](O)=[CH:40][CH:39]=1.CCOC(/N=N/C(OCC)=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([O:1][CH:2]2[CH2:5][C:4]3([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]3)[CH2:3]2)=[CH:40][CH:39]=1

Participants

7

Reactant 5

HCID 46844-ChlorophenolHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 9834677Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 69669804HCID 69669804, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under an inert atmosphere, 0.60 g (2.49 mmoles) of tert-butyl 2-hydroxy-7-aza-spiro[3.5]-nonane-7-carboxylate (WO 2003084948) is dissolved in 25 ml of toluene. 1.024 g (3.90 mmoles) of triphenylphosphine and 0.384 g (2.98 mmoles) of 4-chlorophenol are added. The medium is cooled to 0° C., then a solution of 0.528 g (3.03 mmoles) of diethylazodicarboxylate in 3 ml of toluene is added. The medium is stirred for 14 hrs at ambient temperature then concentrated under vacuum. The residue obtained is taken up in a saturated aqueous solution of sodium carbonate and extracted twice with dichloromethane. The combined organic phases are washed once with a saturated aqueous solution of sodium chloride, dried over sodium sulphate, filtered and concentrated under vacuum. 0.874 g of a residue is obtained, which is used as such in the following stage.

Workup

  1. concentrationthen concentrated under vacuum
  2. customThe residue obtained
  3. extractionextracted twice with dichloromethane
  4. washThe combined organic phases are washed once with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e50e0b4a767f47a6aec3d5527786d710
Source dataset
uspto-grants-2013_03
Patent number
US08394787B2

Reaction notes

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