4-Methylmorpholine → Tert-butyl 2-[[(4-bromobenzoyl)amino]methyl]pyrrolidine-1-carboxylate

HRID 2038969

反応式

HRID 2038969 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH:14][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][C:16]([Br:15])=[CH:17][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 114644-Bromobenzoic acidHCID 2756484(+-)-2-(Aminomethyl)-1-N-Boc-pyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 58185404Tert-butyl 2-[[(4-bromobenzoyl)amino]methyl]pyrrolidine-1-carboxylate収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.00 g, 4.97 mmol) and 4-bromo-benzoic acid (996 mg, 4.97 mmol) in DMF (25 mL) was added N-methylmorpholine (655 μl, 5.96 mmol) and HATU (1.89 g, 4.97 mmol). After stirring for 3 hours the reaction was concentrated then diluted with EtOAc and washed with 1N HCl, saturated NaHCO3, and brine. The organic phase was then dried over Na2SO4 and concentrated. The crude material was purified by silica gel chromatography (20-50% EtOAc-hexanes gradient) to afford 2-[(4-bromo-benzoylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.91 g, 4.97 mmol, quantitative yield). LCMS-ESI+: calc'd for C17H24BrN2O3: 383.1 (M+H+); Found: 383.6 (M+H+).

後処理

  1. concentrationwas concentrated
  2. additionthen diluted with EtOAc
  3. washwashed with 1N HCl, saturated NaHCO3, and brine
  4. dry with materialThe organic phase was then dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography (20-50% EtOAc-hexanes gradient)

出典と根拠

ORDレコード
ord-900dc7948da84e5681cdf89e2d2b1b6d
出典データセット
uspto-grants-2013_11
特許番号
US08575118B2

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