Triethylamine → (S)-4-(4-Bromo-2,5-difluorobenzyl)-3-methylmorpholine

HRID 1924013노트

반응식

HRID 1924013 반응식
[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.Cl.[CH3:13][C@H:14]1[CH2:19][O:18][CH2:17][CH2:16][NH:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClC(Cl)C>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH2:6][N:15]2[CH2:16][CH2:17][O:18][CH2:19][C@@H:14]2[CH3:13])=[C:4]([F:11])[CH:3]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 224890814-Bromo-2,5-difluorobenzaldehydeHCID 53486469(3S)-3-methylmorpholine hydrochloride

생성물 1

HCID 59543858(S)-4-(4-Bromo-2,5-difluorobenzyl)-3-methylmorpholine수율 94.1%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

4-Bromo-2,5-difluorobenzaldehyde (331 mg, 1.5 mmol), (S)-3-methylmorpholine hydrochloride (206 mg, 1.50 mmol) and sodium triacetoxyborohydride (461 mg, 2.18 mmol) were mixed in dichloroethane (5 mL). Triethylamine (0.230 mL, 1.65 mmol) was added and the resulting mixture was stirred at RT under argon atmosphere for 24 h. NaHCO3 (25 mL) was added and the mixture was extracted with dichloromethane (3×25 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated to give (S)-4-(4-bromo-2,5-difluorobenzyl)-3-methylmorpholine (432 mg, 94%) as a solid.

후처리

  1. extractionthe mixture was extracted with dichloromethane (3×25 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7db1490fb085401faa18fa6064368682
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178529B2

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