Triethylamine → Ammonium hydroxide methanol

HRID 270560노트

반응식

HRID 270560 반응식
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][C@@:5]([C:11]([N:13]2[CH2:18][CH2:17][C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])([OH:19])[CH2:15][CH2:14]2)=[O:12])([CH:8]([CH3:10])[CH3:9])[CH2:4]1.[CH3:30][CH:31]1[C:36](=O)[CH2:35][CH2:34][O:33][CH2:32]1.C([N:40](CC)CC)C.[C:45](O[BH-](OC(=O)C)OC(=O)C)(=[O:47])C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH4+:2].[OH-:12].[NH4+:40].[OH-:33].[CH3:45][OH:47].[CH:8]([C@:5]1([C:11]([N:13]2[CH2:18][CH2:17][C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:27])[F:28])([OH:19])[CH2:15][CH2:14]2)=[O:12])[CH2:6][CH2:7][C@@H:3]([NH:2][CH:36]2[CH2:35][CH2:34][O:33][CH2:32][CH:31]2[CH3:30])[CH2:4]1)([CH3:10])[CH3:9]

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 141709263-Methyloxan-4-oneHCID 689309271-{[(1S,3R)-3-amino-1-isopropylcyclopentyl]carbonyl}-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol hydrochloride

생성물 3

HCID 14923Ammonium HydroxideHCID 21894508Ammonium hydroxide methanol수율 1%HCID 68597077HCID 68597077, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-{[(1S,3R)-3-amino-1-isopropylcyclopentyl]carbonyl}-4-[2-(trifluoromethyl)phenyl]piperidin-4-ol hydrochloride (50 mg, 0.1 mmol), 3-methyltetrahydro-4H-pyran-4-one (39 mg, 0.34 mmol), and triethylamine (0.048 mL, 0.34 mmol) in methylene chloride (5 mL) was added sodium triacetoxyborohydride (73 mg, 0.34 mmol). After being stirred overnight at room temperature, a saturated solution of NaHCO3 was added. The solution was extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (0-20% B over 15 min. Bottle A=1% NH4OH/2% MeOH/EtOAc, Bottle B=1% NH4OH/MeOH) afforded the desired product as an oil. MS calculated for C27H39F3N2O3: (M+H) 497; found 497.2.

후처리

  1. extractionThe solution was extracted with methylene chloride three times
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography on silica gel (0-20% B over 15 min

출처 및 근거

ORD 기록
ord-16e8affef9cc44f090a7f58699380b36
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449467B2

반응 노트

불러오는 중…