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

HRID 78942ノート

反応式

HRID 78942 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fc3f7695c62b407ba6438aee8193d995
出典データセット
uspto-grants-2014_09
特許番号
US08841464B2

反応ノート

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