1,2-Dichloroethane → trans-2-(Dibenzylamino)cyclopentanol

HRID 1406044Notes

Reaction equation

HRID 1406044 reaction equation
Cl.N[C@@H:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1O.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])C.C(O[BH-]([O:33][C:34](=O)[CH3:35])OC(=O)C)(=O)C.[Na+].Cl[CH2:39]CCl>ClCCl>[CH2:9]([N:19]([CH2:20][C:21]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:3]=1)[C@@H:22]1[CH2:23][CH2:39][CH2:35][C@H:34]1[OH:33])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 240BenzaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 12886906(1R,2R)-2-aminocyclopentan-1-ol hydrochloride

Product 1

HCID 10085135trans-2-(Dibenzylamino)cyclopentanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-2-aminocyclopentanol hydrochloride (385 mg, 2.82 mmol) in 1,2-dichloroethane was added benzaldehyde (748 mg, 7.04 mmol) and triethylamine (0.51 mL, 3.7 mmol). The mixture was heated to reflux for 2 hours, cooled to room temperature, and sodium triacetoxyborohydride was added. The reaction mixture was heated at reflux for an additional 18 hours, cooled to room temperature, then taken up in dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate solution and with water, then dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 25% to 50% ethyl acetate in heptane) afforded the title compound as a golden oil. Yield: 734 mg, 2.61 mmol, 93%. LCMS m/z 282.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 7.35-7.39 (m, 4H), 7.32 (br dd, J=7.8, 7.2 Hz, 4H), 7.21-7.26 (m, 2H), 4.05-4.12 (m, 1H), 3.79 (d, J=13.9 Hz, 2H), 3.52 (d, J=13.9 Hz, 2H), 2.90-2.99 (m, 1H), 1.74-1.95 (m, 2H), 1.52-1.71 (m, 3H), 1.39-1.49 (m, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for an additional 18 hours
  5. temperaturecooled to room temperature
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification via silica gel chromatography (Gradient: 25% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-cdc7f6f795144ad4945ed3a2e1ae586b
Source dataset
uspto-grants-2014_12
Patent number
US08916564B2

Reaction notes

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