1,3-Diphenyl-2-propanone → (1R)-1,3-diphenyl-1-propanol

HRID 1828058Notes

Reaction equation

HRID 1828058 reaction equation
[C:1]1([CH2:7][C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1)[C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@H](C2)C1.[O:39]1CCCC1>>[C:1]1([C@H:7]([OH:39])[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 75931,3-Diphenyl-2-propanoneHCID 8028Tetrahydrofuran2×HCID 9923113Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane

Product 1

HCID 11845542(1R)-1,3-diphenyl-1-propanolYield 61%

Procedure

A solution of 1,3-diphenylpropanone (1.07 g; 5.09 mmol) in tetrahydrofuran (10 mL) was cooled to −23° C. and treated with an asymmetric reducing agent, (+)-B-chlorodiisopinocampheyl-borane (1.80 g; 5.60 mmol) in 20 mL THF, and the resulting solution was allowed to stand overnight at −23° C. After evaporating to dryness, the residue was treated with ether (65 mL) and diethanolamine (1.0 g) and stirred for 3 hrs. The mixture was then filtered to remove solids and concetrated, and the residue was purified using gradient elution (5% ethyl acetate/hexane to 10% ethyl acetate) on a silica gel column to obtain 660 mg (61%) of (1R)-1,3-diphenyl-1-propanol as a crystalline white solid, 1H NMR (360 Mhz; CDCl3): δ 1.95–2.15 (m, 3H); 2.59–2.78 (m, 2H); 4.65 (dd, 1H, J=5.4, 7.8); 7.14–7.35 (m, 10H).

Workup

  1. additiontreated with
  2. customAfter evaporating to dryness
  3. additionthe residue was treated with ether (65 mL) and diethanolamine (1.0 g)
  4. filtrationThe mixture was then filtered
  5. customto remove solids
  6. customthe residue was purified
  7. washgradient elution (5% ethyl acetate/hexane to 10% ethyl acetate) on a silica gel column

Sources & evidence

ORD record
ord-03dedf35c757456aabf9d72ca12276ed
Source dataset
uspto-grants-2006_06
Patent number
US07056935B2

Reaction notes

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