P-Cresol → HCID 178426866, compound

HRID 634771Notes

Reaction equation

HRID 634771 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([N:21]([CH3:25])[CH2:22][CH2:23][OH:24])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:26]1[C:31](O)=[CH:30][CH:29]=[C:28]([CH3:33])[CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([N:21]([CH3:25])[CH2:22][CH2:23][O:24][C:31]3[CH:30]=[CH:29][C:28]([CH3:33])=[CH:27][CH:26]=3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 2879P-CresolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178484562HCID 178484562, compound

Product 1

HCID 178426866HCID 178426866, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of trans-2-{[4-(4-benzyloxy-phenyl)-cyclohexyl]-methyl-amino}-ethanol (0.3 g, 0.88 mmol), p-cresol (96 mg, 0.88 mmol), triphenylphosphine (232 mg, 0.88 mmol), diethyl-azodicarboxylate (154 mg, 0.88 mmol) and THF was stirred at rt for 3h. The solvent was evaporated and the rsidue was treated with MeOH/H2O (3:1, 50 ml) and hexane (50 ml). The aq. layer was extracted with hexane (30 ml). The combined hexane extracts were dried and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2—MeOH 95:5) to give trans-[4-(4-benzyloxy-phenyl)-cyclohexyl]-methyl-(2-p-tolyloxy-ethyl)-amine (135 mg, 69%, white solid, MS: m/e=430.5 (M+H+)).

Workup

  1. customThe solvent was evaporated
  2. additionthe rsidue was treated with MeOH/H2O (3:1, 50 ml) and hexane (50 ml)
  3. extractionThe aq. layer was extracted with hexane (30 ml)
  4. dry with materialThe combined hexane extracts were dried
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2—MeOH 95:5)

Sources & evidence

ORD record
ord-4ad75fa6c68748989ac99c5a65262ec8
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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