Acetic Acid → Cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-cyano-benzyl)-amine

HRID 78902노트

반응식

HRID 78902 반응식
[CH:1]([C@H:14]1[O:19][CH2:18][C@@H:17]([NH2:20])[CH2:16][CH2:15]1)([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.[C:21]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)#[N:22].C(O)(=O)C.[BH3-]C#N.[Na+]>ClCCCl.CO>[CH:1]([C@H:14]1[O:19][CH2:18][C@@H:17]([NH:20][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([C:21]#[N:22])=[CH:24][CH:25]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11565229Cis-(6-benzhydryl-tetrahydropyran-3-yl)-amine

생성물 1

HCID 66632033Cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-cyano-benzyl)-amine수율 80%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 887Methanol용매

실험 절차

Trans-5-amino-2-diphenylmethyl-tetrahydropyran 15 (0.15 g, 0.56 mmol) was reacted with 4-cyanobenzaldehyde (0.07 g, 0.56 mmol) in the presence of glacial acetic acid (0.033 g, 0.56 mmol) in 1,2-dichloroethane (20 ml), and NaCNBH3 (0.042 g, 0.67 mmol) in methanol (5 ml) (Procedure D) to give compound 16c (0.17 g, 80%) as an oil.

출처 및 근거

ORD 기록
ord-542a5cf848c44fc7b63110e8f0d42fc5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841464B2

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