Potassium tert-butoxide → tert-Butyl 4-[(1R,2R)-1-(4-chlorophenyl)-1-hydroxypentan-2-yl]benzoate

HRID 2408149Notes

Reaction equation

HRID 2408149 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:32])[CH:15]([C:19]2[CH:31]=[CH:30][C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:21][CH:20]=2)[CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=1.[H][H]>CC(O)C>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C@H:14]([OH:32])[C@@H:15]([C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])=[CH:30][CH:31]=2)[CH2:16][CH2:17][CH3:18])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 58349443tert-Butyl 4-(1-(4-chlorophenyl)-1-oxopentan-2-yl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 58349469tert-Butyl 4-[(1R,2R)-1-(4-chlorophenyl)-1-hydroxypentan-2-yl]benzoate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To degassed 2-propanol (5.0 mL) was added RuCl2-[(8)-xyl-SEGPHOS][(S)-DAIPEN] (16.2 mg, 0.0134 mmol) and potassium t-butoxide (300 mg, 2.67 mmol). After this mixture was stirred at room temperature for 2 hours, the material obtained in Step A was added in 2-propanol (25 mL). This mixture was then treated with hydrogen (100 psi) at room temperature for 18 hours. The mixture was concentrated, then the residue was recrystallized from IPA/water to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 7.96 (m, 2H), 7.32 (m, 2H), 7.26 (m, 2H), 7.22 (m, 2H), 4.76 (dd, J=7.7, 2.9 Hz, 1H), 2.89 (ddd, J=11.5, 7.7, 4.2 Hz, 1H), 1.84 (d, J=2.9 Hz, 1H), 1.62 (s, 9H), 1.61 (m, 1H), 1.41 (m, 1H), 1.05 (m, 2H), 0.76 (t, J=7.3 Hz, 3H); LC2: 2.38 min. (M−H2O-tBu+H)+ 301; Chiral SFC Method: Chiralpak AD-H (250×4.6 mm), isocratic 15% MeOH/CO2, 1.5 mL/min, 200 bar, 35° C., 215 nm, 15 minutes: desired alcohol retention time=9.8 min; enantiomeric alcohol, retention time=10.6 min; diastereomeric alcohols retention times=5.2 and 6.3 min.

Workup

  1. customTo degassed 2-propanol (5.0 mL)
  2. concentrationThe mixture was concentrated
  3. customthe residue was recrystallized from IPA/water

Sources & evidence

ORD record
ord-9db4d4462b14429d8f8bbac8f420825e
Source dataset
uspto-grants-2014_08
Patent number
US08809579B2

Reaction notes

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