Triethylamine → HCID 178453892, 화합물

HRID 72848

반응식

HRID 72848 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:6]=2[CH:16]=1.[C:17]([O:21][C:22](=[O:33])[NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][CH:31]=O)[CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:17]([O:21][C:22](=[O:33])[NH:23][C@H:24]1[CH2:25][CH2:26][C@H:27]([CH2:30][CH2:31][N:13]2[CH2:12][CH2:11][CH:10]([C:7]3[C:6]4[CH:16]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[O:9][N:8]=3)[CH2:15][CH2:14]2)[CH2:28][CH2:29]1)([CH3:20])([CH3:19])[CH3:18]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 27947555-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazoleHCID 5049666Sodium triacetoxyborohydrideHCID 178453924HCID 178453924, 화합물2회

생성물 1

HCID 178453892HCID 178453892, 화합물수율 102%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A mixture of 5-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (1.3 g, 5 mmol), trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (example 1, intermediate C) (1.6 g, 6 mmol), triethylamine (0.64 mL, 5 mmol) in 1,2 dichloroethane (27 mL) was stirred for 4 h at room temperature and sodium triacetoxyborohydride (1.9 g, 9 mmol) was added slowly and the resulting solution was stirred for 12 hours until the TLC indicated completion of the reaction. The mixture was filtrated and concentrated to dryness and purified with column chromatography on silica gel using CH2Cl2—CH2Cl2/MeOH (1-9:1). The product fractions were concentrated to give 2.3 g (5.1 mmol, 100% yield) of a off-white solid. MS (m/e): 446.3 (M+H+).

후처리

  1. stirringthe resulting solution was stirred for 12 hours until the TLC
  2. customcompletion of the reaction
  3. filtrationThe mixture was filtrated
  4. concentrationconcentrated to dryness
  5. custompurified with column chromatography on silica gel
  6. concentrationThe product fractions were concentrated

출처 및 근거

ORD 기록
ord-376f96ff0f514fed88ddc6e5c17bd469
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829029B2

연결된 노트

불러오는 중…