tert-Butanol → (2S,3S)-1-tert-Butoxycarbonyl-3-(2-methoxybenzyl)amino-2-phenylpiperidine

HRID 1856772ノート

反応式

HRID 1856772 の反応式
Cl.Cl.[CH3:3][O:4][C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[CH2:7][NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][C@H:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+].O(OC(C(C)(C)C)=O)[O:28][C:29](C(C)(C)C)=O.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:29]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:9]([NH:8][CH2:7][C:6]2[CH:21]=[CH:22][CH:23]=[CH:24][C:5]=2[O:4][CH3:3])[C@@H:10]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:28])([CH3:45])([CH3:44])[CH3:43]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 14215521(tBuOCO)2OHCID 68466923CP 99994 dihydrochloride

生成物 1

HCID 11223212(2S,3S)-1-tert-Butoxycarbonyl-3-(2-methoxybenzyl)amino-2-phenylpiperidine

実験手順

To a stirred and ice-cooled mixture of Compound 3 (10.0 g, 27.1 mmol), 3.0 M NaOH aq. (36.1 ml, 108.4 mmol) and tert-BuOH (15.0 ml) was added (tert-BuOCO)2O (Boc2O, 7.39 g, 33.8 mmol). After stirring at room temperature overnight, the mixture was extracted with AcOEt (x3). The combined AcOEt extracts were washed with sat. NaHCO3 and brine, dried over Na2SO4, and concentrated to give Compound 4 (11.3 g, quant.) as a pale yellow syrup.

後処理

  1. temperatureice-cooled
  2. stirringAfter stirring at room temperature overnight
  3. extractionthe mixture was extracted with AcOEt (x3)
  4. washThe combined AcOEt extracts were washed with sat. NaHCO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-bb619cae5f0a4c1da9253b0ead3507c2
出典データセット
uspto-grants-2000_11
特許番号
US06143767

反応ノート

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