2-Benzhydryl-3-quinuclidinone → (2S,3S)-2-benzhydrylquinuclidin-3-ol

HRID 409652

反応式

HRID 409652 の反応式
[CH:1]([CH:14]1[C:19](=[O:20])[CH:18]2[CH2:21][CH2:22][N:15]1[CH2:16][CH2:17]2)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[H][H]>CC(O)C>[CH:1]([C@H:14]1[C@@H:19]([OH:20])[CH:18]2[CH2:17][CH2:16][N:15]1[CH2:22][CH2:21]2)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

5

反応物 3

HCID 4251102-Benzhydryl-3-quinuclidinoneHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 10613679(2S,3S)-2-benzhydrylquinuclidin-3-ol収率 97%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒3 回

実験手順

398.0 mg (1.30 mmol) of a racemic mixture of 2-benzhydrylquinuclidin-3-one (1-2), 1.1 mg (1.3 μmol) of {[(S)-(6,6′-dimethyl-1,1′-biphenyl-2,2′-diyl)-bis(diphenylphosphine)]ruthenium (II) dichloride (DMF)n} complex, 6.4 ml of 2-propanol and 31 μl (1.55 μmol) of a 0.05 M 2-propanol solution of (2R,3R,4R,5R)-3,4-O-isopropylidenehexane-2,5-diamine were added to an autoclave in which the inside had been replaced with argon followed by degassing and stirring for 30 minutes at room temperature. 0.13 mL (0.13 mmol) of a 2-propanol solution of potassium tert-butoxide (1.0 M) were added thereto followed by stirring for 18 hours at 20 to 25° C. at a hydrogen pressure of 1 MPa. The same post-treatment procedure as Example 7 was carried out to obtain (2S,3S)-2-benzhydrylquinuclidin-3-ol (3-2) at a yield of 97% and optical purity of >99% ee.

後処理

  1. customby degassing

出典と根拠

ORDレコード
ord-1916bbe51b7f4585836777c1dc4af8b8
出典データセット
uspto-grants-2014_06
特許番号
US08759524B2

関連ノート

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