4-Hydroxybenzaldehyde → (2S,4R,5R)-2-benzhydryl-5-(4-hydroxy-benzylamino)-tetrahydropyran-4-ol

HRID 78942노트

반응식

HRID 78942 반응식
[NH2:1][C@@H:2]1[CH2:7][O:6][C@H:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][C@H:3]1[OH:21].[OH:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.C(O)(=O)C.[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.CO.O>[CH:8]([C@@H:5]1[CH2:4][C@@H:3]([OH:21])[C@H:2]([NH:1][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([OH:22])=[CH:24][CH:25]=2)[CH2:7][O:6]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

9

반응물 5

HCID 1264-HydroxybenzaldehydeHCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 11514718(2S,4R,5R)-5-amino-2-benzhydryl-tetrahydro-pyran-4-ol

생성물 1

HCID 11552844(2S,4R,5R)-2-benzhydryl-5-(4-hydroxy-benzylamino)-tetrahydropyran-4-ol

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 887Methanol용매HCID 962Water용매

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온도
0 °C

실험 절차

To a solution of (2S,4R,5R)-5-amino-2-benzhydryl-tetrahydro-pyran-4-ol 31a (0.02 g, 0.09 mmol), 4-hydroxybenzaldehyde (0.01 g, 0.09 mmol) and glacial acetic acid (0.005 g, 0.09 mmol) in 1,2-dichloroethane (5 ml) was added portionwise NaCNBH3 (0.007 g, 0.11 mmol) in methanol (1 ml). The reaction was continued for 4 hr. Water was added to quench the reaction and the mixture was stirred for 30 minutes at 0° C. The reaction mixture was stirred with saturated aqueous NaHCO3 and the product was extracted with methylene chloride (3×10 ml). The combined organic phases were washed with brine, water and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure, and the residue was purified by flash chromatography (Hexane/Ethyl Acetate/Triethylamine 3:2:0.2) to give (2S,4R,5R)-2-benzhydryl-5-(4-hydroxy-benzylamino)-tetrahydropyran-4-ol, (−)-32a, 0.03 g (80%, [α]D=(−)72.6, c=1, MeOH).

후처리

  1. customto quench
  2. customthe reaction
  3. extractionthe product was extracted with methylene chloride (3×10 ml)
  4. washThe combined organic phases were washed with brine, water
  5. dry with materialdried over anhydrous Na2SO4
  6. customSolvent was removed under reduced pressure
  7. customthe residue was purified by flash chromatography (Hexane/Ethyl Acetate/Triethylamine 3:2:0.2)

출처 및 근거

ORD 기록
ord-fc3f7695c62b407ba6438aee8193d995
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841464B2

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