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

HRID 730641ノート

反応式

HRID 730641 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-196fc458c08140fa9742debef6d445a4
出典データセット
uspto-grants-2009_09
特許番号
US07582625B2

反応ノート

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