Acetic Acid → Benzyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperazine-1-carboxylate

HRID 419427ノート

反応式

HRID 419427 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N:15]1([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:5][C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:18]2[CH2:17][CH2:16][N:15]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:20][CH2:19]2)[CH2:10][CH2:9]1)=[O:2])([CH3:7])[CH3:6]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 643495Benzyl piperazine-1-carboxylateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 18971584Benzyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yl)piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Combined 1-boc-4-piperidone (10.0 g, 50.2 mmol), benzyl 1-piperazine-carboxylate (19.3 mL, 100.4 mmol), HOAc (4.3 mL, 75.3 mmol) and TEA (7.0 mL, 50.2 mmol) in DCE (150 mL) were stirred at rt. Sodium triacetoxyborohydride was added (16.0 g, 75.3 mmol). The reaction was stirred for 3 h at which point TLC shows starting material is consumed. The reaction was quenched with NaHCO3 and extracted with DCM (3×). Combined organics were dried over MgSO4, filtered and concentrated in vacuo. Diluted crude material with DCM and adsorbed onto a prepacked silica gel solid loading cartridge and purified by column chromatography to give title compound of step A (yield not obtained). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.04-7.52 (m, 5H), 5.02 (s, 2H), 3.74-4.05 (m, 2H), 3.06-3.49 (m, 4H), 2.63 (br. s., 2H), 2.22-2.50 (m, 5H), 1.64 (d, J=12.1 Hz, 2H), 1.07-1.27 (m, 2H), 1.34 (s, 9H).

後処理

  1. customis consumed
  2. customThe reaction was quenched with NaHCO3
  3. extractionextracted with DCM (3×)
  4. dry with materialCombined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. additionDiluted crude material with DCM
  8. custompurified by column chromatography

出典と根拠

ORDレコード
ord-a0b92b8580a845768f3d34aedfb86f7a
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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