Phenol → HCID 67486365, compound

HRID 1809996Notes

Reaction equation

HRID 1809996 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:15][CH2:16][CH2:17][OH:18])[C@H:8]1[CH2:13][CH2:12][C@H:11]([CH3:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:20]1(O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:19])[N:7]([CH:8]1[CH2:9][CH2:10][CH:11]([CH3:14])[CH2:12][CH2:13]1)[CH2:15][CH2:16][CH2:17][O:18][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178453537HCID 178453537, compound

Product 1

HCID 67486365HCID 67486365, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3-Hydroxy-propyl)-(trans-4-methyl-cyclohexyl)-carbamic acid tert-butyl ester (1.5 g, 5.53 mmol) and phenol (0.52 g, 5.53 mmol) in dry THF (15 mL) was added DEAD (1.06 g, 6.08 mmol) and resin bound triphenyl phosphine (polystyrene, 2% cross linking, loading=3 mmol/g, 2.76 g). The reaction mixture was gently stirred for 18 h before the resin was filtered off and washed with THF (2×15 mL). The fitrate was concentrated in vacuo and the resulting residue was purified (SiO2, 0-20% EtOAc in heptane) to give 0.99 g of (4-methyl-cyclohexyl)-(3-phenoxy-propyl)-carbamic acid tert-butyl ester. This was dissolved in DCMTFA ((3:1), 16 mL) and the mixture was stirred for 18 h before the solvent was removed in vacuo to give 0.75 g of the TFA salt of (4-methyl-cyclohexyl)-(3-phenoxy-propyl)-amine.

Workup

  1. filtrationwas filtered off
  2. washwashed with THF (2×15 mL)
  3. concentrationThe fitrate was concentrated in vacuo
  4. customthe resulting residue was purified (SiO2, 0-20% EtOAc in heptane)

Sources & evidence

ORD record
ord-bd4529c1317a4128a0d9c9a3e828bc73
Source dataset
uspto-grants-2013_01
Patent number
US08362049B2

Reaction notes

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