Cyclohexanol → HCID 18477124, compound

HRID 2188213Notes

Reaction equation

HRID 2188213 reaction equation
[CH2:1]([CH2:8][NH:9][CH2:10][C:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:21])[CH:17]=2)[C:12]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]1(O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:1]([CH2:8][NH:9][CH2:10][C:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:17]=2)[C:12]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18477100HCID 18477100, compound

Product 1

HCID 18477124HCID 18477124, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(N-benzylmethylamino)methyl-6-hydroxy-1-phenyl-3,4-dihydronaphthalene (0.53 g), cyclohexanol (0.26 cm3), triphenylphosphine (0.579 g) and tetrahydrofuran (20 cm3), was added diethyl azodicarboxylate (0.35 cm3) at room temperature. After stirring for 5 h the solvent was removed under reduced pressure. The crude product was purified by column chromatography [silica, eluting with ethyl acetate-heptane (1:4)] to yield the title compound (0.442 g) as a yellow oil.

Workup

  1. customwas removed under reduced pressure
  2. customThe crude product was purified by column chromatography [silica, eluting with ethyl acetate-heptane (1:4)]

Sources & evidence

ORD record
ord-5083437a1cd440759af9fe86620f3e62
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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