Triphenylphosphine → HCID 66629762, compound

HRID 555383Notes

Reaction equation

HRID 555383 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[CH2:8]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:40]([O:42][C:43]([CH:45]1[CH2:50][CH2:49][CH:48](O)[CH2:47][CH2:46]1)=[O:44])[CH3:41].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:40]([O:42][C:43]([CH:45]1[CH2:50][CH2:49][CH:48]([O:19][C:16]2[CH:15]=[CH:14][C:13]([C:12](=[O:20])[NH:11][CH:2]3[CH:3]4[CH2:9][CH:7]5[CH2:6][CH:5]([CH2:10][CH:1]3[CH2:8]5)[CH2:4]4)=[CH:18][CH:17]=2)[CH2:47][CH2:46]1)=[O:44])[CH3:41]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 5462977Diethyl azodicarboxylateHCID 66630625HCID 66630625, compound

Product 1

HCID 66629762HCID 66629762, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-adamantan-2-yl-4-hydroxy-benzamide (6 g, 22.11 mmol) in dry THF (100 mL) was added triphenyl phosphine (8.7 g, 33.17 mmol) and 4-hydroxy cyclo-hexane carboxylic acid ethyl ester (4.57 g, 26.53 mmol). The reaction mixture was cooled to 0° C. and DEAD (5.22 mL, 33.17 mmol) was added dropwise from an addition funnel over a period of 30 min. The reaction was gradually brought to room temperature and stirring continued for 48 hrs. The solvent was removed under vacuum and ether (100 mL) was added and cooled to 0° C. The solid formed was filtered off and the clear filtrate concentrated and purified by column chromatography (Gyan-flash). Desired fractions were collected and the solvent evaporated. The residue was crystallised from diethyl ether and filtered off affording 3 g (32%) of 4-[4-(adamantan-2-ylcarbamoyl)-phenoxy]-cyclohexane carboxylic acid ethyl ester as a solid.

Workup

  1. customwas gradually brought to room temperature
  2. customThe solvent was removed under vacuum and ether (100 mL)
  3. additionwas added
  4. temperaturecooled to 0° C
  5. customThe solid formed
  6. filtrationwas filtered off
  7. concentrationthe clear filtrate concentrated
  8. custompurified by column chromatography (Gyan-flash)
  9. customDesired fractions were collected
  10. customthe solvent evaporated
  11. customThe residue was crystallised from diethyl ether
  12. filtrationfiltered off

Sources & evidence

ORD record
ord-be25847febdc45d8b7d9e026aba4c80e
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

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