Sodium triacetoxyborohydride → 4-[((1R,3S)-3-Isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)amino]-1-pyrimidin-2-ylcyclohexanol

HRID 969568노트

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HRID 969568 반응식
[OH:1][C:2]1([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH:15]([C@:18]1([C:24]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][C:30]([C:36]([F:39])([F:38])[F:37])=[CH:31][CH:32]=3)[CH2:27]2)=[O:25])[CH2:22][CH2:21][C@@H:20]([NH2:23])[CH2:19]1)([CH3:17])[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:15]([C@:18]1([C:24]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][C:30]([C:36]([F:39])([F:37])[F:38])=[CH:31][CH:32]=3)[CH2:27]2)=[O:25])[CH2:22][CH2:21][C@@H:20]([NH:23][CH:5]2[CH2:6][CH2:7][C:2]([C:9]3[N:14]=[CH:13][CH:12]=[CH:11][N:10]=3)([OH:1])[CH2:3][CH2:4]2)[CH2:19]1)([CH3:17])[CH3:16]

참가 물질

5

반응물 3

HCID 5049666Sodium triacetoxyborohydride2회HCID 58784490((1S,3R)-3-amino-1-isopropylcyclopentyl)(7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl)methanoneHCID 590174304-Hydroxy-4-pyrimidin-2-yl-cyclohexanone

생성물 1

HCID 115046884-[((1R,3S)-3-Isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentyl)amino]-1-pyrimidin-2-ylcyclohexanol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-hydroxy-4-pyrimidin-2-yl-cyclohexanone (59.8 mg, 0.31 mmol) and (1R,3S)-3-isopropyl-3-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]carbonyl}cyclopentanamine (110 mg, 0.31 mmol) of Step C-2 of Example 1 in CH2Cl2(10 mL) was added sodium triacetoxyborohydride (131 mg, 0.62 mmol). After being stirred overnight, more sodium triacetoxyborohydride was added to bring the equivalents of the reducing agent to 5 equivalents. After stirring for another 5 hrs, the reaction was quenched with aqueous NaOH. The resulting solution was extracted with EtOAc three times. The combined extracts were dried over MgSO4 and concentrated. Purification by flash chromatography followed by HPLC gave two isomers. Isomer 1 and isomer 2: MS calculated for C29H37F3N4O2: (M+H)+531; found 531.1.

후처리

  1. stirringAfter stirring for another 5 hrs
  2. customthe reaction was quenched with aqueous NaOH
  3. extractionThe resulting solution was extracted with EtOAc three times
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customPurification by flash chromatography
  7. customgave two isomers

출처 및 근거

ORD 기록
ord-bf1f05c5205b4b37a683c010801c4fa6
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307086B2

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