Acetic Acid → 1-(3-tert-Butoxycarbonylamino-benzyl)-piperidine-4-carboxylic acid ethyl ester

HRID 1486689ノート

反応式

HRID 1486689 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]=O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH:17]1[CH2:27][CH2:26][CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:18]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.O>[CH2:24]([O:23][C:21]([CH:20]1[CH2:26][CH2:27][N:17]([CH2:14][C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:16])[CH:9]=2)[CH2:18][CH2:19]1)=[O:22])[CH3:25]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 70770Ethyl 4-piperidinecarboxylateHCID 5003444Sodium cyanoborohydrideHCID 167407363-(BOC-Amino)benzaldehyde

生成物 1

HCID 867065211-(3-tert-Butoxycarbonylamino-benzyl)-piperidine-4-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of (3-formyl-phenyl)-carbamic acid tert-butyl ester (Schadendorf T et al., Tetrahedron Letters (2007), 48(51), 9044-9047), (1 g, 4.52 mmol), ethyl isonipecotate (800 mg, 5.09 mmol) and TEA (0.7 mL, 5 mmol) in MeOH (50 mL) is treated with acetic acid (1.03 mL, 18 mmol) and stirred at RT for 2 h. Sodium cyanoborohydride (398 mg, 6.33 mmol) is added at once and the reaction mixture is stirred for 18 h at RT. Water (5 mL) is added to the mixture and the solvents are evaporated. The residue is partitioned between diethyl ether (50 mL) and aqueous 0.1N HCl (50 mL). The aqueous phase is separated, washed twice with diethyl ether (25 mL) and basified with 1N NaOH solution (10 mL). The aqueous phase is extracted three times with DCM (3×50 mL). The combined organic phases are dried over MgSO4 and evaporated. The title compound is obtained as a thick oil; LC-MS A: tR=0.71 min; [M+H]+=363.48.

後処理

  1. stirringis stirred for 18 h at RT
  2. customthe solvents are evaporated
  3. customThe residue is partitioned between diethyl ether (50 mL) and aqueous 0.1N HCl (50 mL)
  4. customThe aqueous phase is separated
  5. washwashed twice with diethyl ether (25 mL)
  6. extractionThe aqueous phase is extracted three times with DCM (3×50 mL)
  7. dry with materialThe combined organic phases are dried over MgSO4
  8. customevaporated

出典と根拠

ORDレコード
ord-d53e229b4f10439d9d01db4433951973
出典データセット
uspto-grants-2016_08
特許番号
US09428456B2

反応ノート

読み込み中…