Sodium Hydroxide → Ethyl([1,4']bipiperidinyl-4-yloxy)-acetate

HRID 730641노트

반응식

HRID 730641 반응식
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O=[C:16]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]1.[NH:29]1[CH2:34][CH2:33][CH:32]([O:35][CH2:36][C:37]([O:39][C:40]([CH3:43])(C)C)=[O:38])[CH2:31][CH2:30]1.[OH-].[Na+]>C1COCC1>[N:29]1([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:30][CH2:31][CH:32]([O:35][CH2:36][C:37]([O:39][CH2:40][CH3:43])=[O:38])[CH2:33][CH2:34]1

참가 물질

6

반응물 4

HCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 10036224Tert-butyl (piperidin-4-yloxy)-acetate

생성물 1

HCID 57807779Ethyl([1,4']bipiperidinyl-4-yloxy)-acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2.90 g (13.3 mmol) NaBH(OAc)3 were added batchwise to a solution of 2.58 g (11.1 mmol)) tert. butyl 4-oxo-piperidine-1-carboxylate and 2.80 g (12.4 mmol) tert. butyl (piperidin-4-yloxy)-acetate in 30 mL THF and the reaction mixture was stirred overnight at RT. 50 mL of 1 M NaOH was added, the mixture was stirred for 1 h at RT, extracted exhaustively with EtOAc and the combined organic phases were dried on Na2SO4. After the elimination of the desiccant and solvent the residue was purified by chromatography (Alox, activity stage II-III, DCM/MeOH 100:1).

후처리

  1. stirringthe mixture was stirred for 1 h at RT
  2. extractionextracted exhaustively with EtOAc
  3. customthe combined organic phases were dried on Na2SO4
  4. customAfter the elimination of the desiccant and solvent the residue was purified by chromatography (Alox, activity stage II-III, DCM/MeOH 100:1)

출처 및 근거

ORD 기록
ord-196fc458c08140fa9742debef6d445a4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582625B2

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