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

HRID 977230노트

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HRID 977230 반응식
[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

참가 물질

4

반응물 3

HCID 75931,3-Diphenyl-2-propanoneHCID 8028Tetrahydrofuran2회HCID 9923113Chlorobis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo(3.1.1)hept-3-yl)borane

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-78d2c4542d964bf4a5b9c2842ceb0fdb
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614547

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