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

HRID 977230ノート

反応式

HRID 977230 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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 concentrated, 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): d 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).

後処理

  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. concentrationconcentrated
  7. customthe residue was purified
  8. washgradient elution (5% ethyl acetate/hexane to 10% ethyl acetate) on a silica gel column

出典と根拠

ORDレコード
ord-78d2c4542d964bf4a5b9c2842ceb0fdb
出典データセット
uspto-grants-1997_03
特許番号
US05614547

反応ノート

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