Hydrochloric Acid → 1-Amino-3-(cholestan-3-yloxy)-propane

HRID 74861

Reaction equation

HRID 74861 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][CH:18]([O:28][CH2:29][CH2:30][C:31]#[N:32])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].C(Cl)(Cl)Cl.CCO.Cl>C1(C)C=CC=CC=1.O.[Pt]=O>[NH2:32][CH2:31][CH2:30][CH2:29][O:28][CH:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[CH:16]([CH2:15][CH2:14][C@@H:13]3[C@@H:23]2[CH2:24][CH2:25][C@@:26]2([CH3:27])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:17]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6212ChloroformHCID 674348303-(Cholestan-3-yloxy)propanenitrile

Product 1

HCID 674336311-Amino-3-(cholestan-3-yloxy)-propane

Reagents, catalysts & solvents 2

HCID 86587499Platinum oxide monohydrateCatalystHCID 1140TolueneSolvent

Procedure

3-(Cholestan-3-yloxy)propanenitrile 135 (442 mg, 1 mmol) was taken up in a mixture of toluene (1 mL), chloroform (1.5 mL), EtOH (1 mL) and conc. HCl (200 μL). Platinum oxide hydrate (46 mg) was added. The mixture was stirred under hydrogen (80 psi) at room temperature for 48 hours. The solvent was evaporated and the residue taken up with DCM (40 mL) and NaHCO3 (sat.) (40 mL). The organic phase was separated and washed with NaHCO3 (sat.) (30 mL), followed by brine (20 mL), before being dried (Na2SO4) and the solvent evaporated to yield the white foam product which was reacted on without further purification or characterization.

Workup

  1. customThe solvent was evaporated
  2. customThe organic phase was separated
  3. washwashed with NaHCO3 (sat.) (30 mL)
  4. dry with materialbefore being dried (Na2SO4)
  5. customthe solvent evaporated
  6. customto yield the white foam product which
  7. customwas reacted on without further purification or characterization

Sources & evidence

ORD record
ord-8d1a18749b7445aa82209e3c4e390308
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Linked notes

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