Tetrahydrofuran → Benzyl 4-tert-butoxycarbonylmethoxy-[1,4']bipiperidinyl-1'-carboxylate

HRID 599737ノート

反応式

HRID 599737 の反応式
[BH-](O[C:11]([CH3:13])=O)(OC(C)=O)OC(C)=O.[Na+].O=[C:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])(C)C)=[O:23])[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])([CH3:42])[CH3:41])=[O:38])[CH2:31][CH2:30]1.[OH-].[Na+].[CH2:46]1[CH2:50]OC[CH2:47]1>>[C:40]([O:39][C:37]([CH2:36][O:35][CH:32]1[CH2:31][CH2:30][N:29]([CH:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][CH2:25][C:28]3[CH:13]=[CH:11][CH:50]=[CH:46][CH:47]=3)=[O:23])[CH2:20][CH2:21]2)[CH2:34][CH2:33]1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

参加物

6

反応物 5

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 10036224Tert-butyl (piperidin-4-yloxy)-acetate

生成物 1

HCID 66941898Benzyl 4-tert-butoxycarbonylmethoxy-[1,4']bipiperidinyl-1'-carboxylate

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-7859b5c8cf4d4bbf9d79796c1d0ed312
出典データセット
uspto-grants-2011_03
特許番号
US07897603B2

反応ノート

読み込み中…