Methanol → (R)-1-(3-Tert-butyloxycarbonylphenyl)ethanol

HRID 2300770Notes

Reaction equation

HRID 2300770 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])(=[O:3])[CH3:2].CO>C(Cl)Cl>[C:10]([O:9][C:7]([C:6]1[CH:5]=[C:4]([C@H:1]([OH:3])[CH3:2])[CH:16]=[CH:15][CH:14]=1)=[O:8])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 887MethanolHCID 46941403tert-Butyl 3-acetylbenzoate

Product 1

HCID 69964056(R)-1-(3-Tert-butyloxycarbonylphenyl)ethanolYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a dry flask under nitrogen, (S)-oxazaborolidine (4.81 mmol) was dissolved in dry CH2Cl2 (12 mL). This solution was maintained between −20° C. and −25° C. as a solution of tert-butyl (3-acetyl)benzoate (4.20 mmol) in dry CH2Cl2 (12 mL) was added dropwise over 20 minutes. The reaction mixture was then allowed to warm to room temperature for 45 minutes. This mixture was then cooled to −78° C. and methanol (20 mL) added dropwise. The mixture was allowed to warm to room temperature. Solvent was removed under reduced pressure then the residue dissolved in methanol and concentrated under reduced pressure twice more. The dried residue was purified by silica gel chromatography in 10-30% ethyl acetate/hexanes to yield 865 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 8.00 (m, 1H); 7.92 (m, 1H); 7.58 (d, J=7.5 Hz, 1H); 7.42 (t, J=7.7 Hz, 1H); 4.98 (m, 1H); 1.62 (s, 9H); 1.54 (d, J=6.4 Hz, 3H).

Workup

  1. additionwas added dropwise over 20 minutes
  2. temperatureThis mixture was then cooled to −78° C.
  3. temperatureto warm to room temperature
  4. customSolvent was removed under reduced pressure
  5. dissolutionthe residue dissolved in methanol
  6. concentrationconcentrated under reduced pressure twice more
  7. customThe dried residue was purified by silica gel chromatography in 10-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c3f89156c3ff47baa367b34071f557d1
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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