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

HRID 1924013ノート

反応式

HRID 1924013 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7db1490fb085401faa18fa6064368682
出典データセット
uspto-grants-2012_05
特許番号
US08178529B2

反応ノート

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