Diisopropylethylamine → (R)-3-(5-bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1094255ノート

反応式

HRID 1094255 の反応式
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Br:15][C:16]1[CH:17]=[N:18][C:19](Cl)=[N:20][CH:21]=1.CCN(C(C)C)C(C)C.CC(=O)OCC.CCCCCCC>CCO.CC(=O)OCC>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([NH:1][C:19]2[N:20]=[CH:21][C:16]([Br:15])=[CH:17][N:18]=2)[CH2:3]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 21899848Ethylacetate heptane

生成物 1

HCID 66639558(R)-3-(5-bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester収率 48%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (R)-3-amino-1-N-Boc-piperidine (920 mg) in dry EtOH (20 mL) were added successively 5-bromo-2-chloropyrimidine (957 mg), DIEA (0.86 mL). The reaction mixture was stirred at reflux for 16 hours under nitrogen. After cooling to RT, the reaction mixture was diluted with EA, washed with sat. NaHCO3, 1N NaOH. The organic extract was dried (MgSO4), filtered and concentrated to yield a crude brown-orange oil. FC (EA/n-heptane: 2/8) gave 787 mg (48%) of the title compound as a light brown solid.

後処理

  1. temperatureat reflux for 16 hours under nitrogen
  2. washwashed with sat. NaHCO3, 1N NaOH
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude brown-orange oil

出典と根拠

ORDレコード
ord-bc11a06f67ad407e8f83f67990e20913
出典データセット
uspto-grants-2012_03
特許番号
US08133901B2

反応ノート

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