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

HRID 409652

반응식

HRID 409652 반응식
[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

참가 물질

5

반응물 3

HCID 4251102-Benzhydryl-3-quinuclidinoneHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매3회

실험 절차

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.

후처리

  1. customby degassing

출처 및 근거

ORD 기록
ord-1916bbe51b7f4585836777c1dc4af8b8
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759524B2

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