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Diisopropylethylamine → Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate

HRID 736413
ノート
印刷プレビュー

反応式

HRID 736413 の反応式
C(N1C2C=CC=CC=2N([C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3([C:29]([OH:31])=[O:30])[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:19][CH2:18]2)=[O:14])C1=O)(C)C.N1CCC(CNC(=O)[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])CC1.[CH3:48]CN(C(C)C)C(C)C>CN1CCCC1=O.C([O-])(O)=O.[Na+]>[C:43]([O:42][C:13]([NH:15][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([CH2:23][C:24]2([C:29]([O:31][CH3:48])=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:21][CH2:22]1)=[O:14])([CH3:46])([CH3:45])[CH3:44]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 115105321-{[4-({[(3-isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}cyclopentanecarboxylic acid

生成物 1

HCID 67232469Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate収率 67.2%

試薬・触媒・溶媒 2

HCID 13387
N-methyl-2-pyrrolidone
溶媒
HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
120 °C

実験手順

A mixture of Methyl 1-(iodomethyl)cyclopentanecarboxylate (5.52 g, 0.0206 mol, Step 1), tert-butyl (piperidin-4-ylmethyl)carbamate (8.83 g, 0.0412 mol) and iPr2NEt (10.76 mL, 0.0618 mol) in N-methylpyrrolidone (70 mL) was stirred at 120° C. for 24 h. After cooling, the reaction mixture was diluted with sat. NaHCO3 aq. (200 mL), extracted with AcOEt (200 mL) for three times, and the combined organic layer was washed with water (200 mL) and brine (200 mL). The organic layer was dried over Na2SO4, filtered and concentrated. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1) to give 4.91 g (67%) of title compound as a yellow syrup.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with AcOEt (200 mL) for three times
  3. washthe combined organic layer was washed with water (200 mL) and brine (200 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customRemoval of the solvent
  8. customgave a residue, which
  9. customwas chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1)

出典と根拠

ORDレコード
ord-df2cbae2cf924e569589faf7c96324f7
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07595329B2

反応ノート

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