Azetidine → tert-Butyl 4-[(azetidin-1-yl)carbonyl]piperidine-1-carboxylate

HRID 426083ノート

反応式

HRID 426083 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:19]([CH:23]([CH3:25])C)[CH:20](C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.N1CCC1>CN(C=O)C.C(Cl)Cl>[N:19]1([C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])[CH2:20][CH2:25][CH2:23]1

参加物

7

反応物 4

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

生成物 1

HCID 23658779tert-Butyl 4-[(azetidin-1-yl)carbonyl]piperidine-1-carboxylate収率 106.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

1-(tert-Butoxycarbonyl)piperidine-4-carboxylic acid (0.40 g, 1.75 mmol) was dissolved in dry DMF (5 mL) and to the solution were added DIPEA (1.22 mL, 7.0 mmol), TBTU (0.67 g, 2.1 mmol) and azetidine (0.12 g, 2.1 mmol). The reaction mixture was stirred at RT for 12 h. The mixture was diluted with methylene chloride and then washed with an aqueous solution of HCl (2 M) and then with an aqueous solution of NaHCO3 (sat.). The phases were separated by means of a phase separator column and the solvent was removed by evaporation. There was obtained 0.50 g (100%) of tert-butyl 4-(azetidin-1-ylcarbonyl)piperidine-1-carboxylate as a crude solid. 1H NMR (500 MHz, CDCl3): 1.4-1.5 (s, 9H), 1.6-1.9 (m, 5H), 2.2-2.4 (m, 3H), 2.6-2.8 (m, 2H), 3.9-4.2 (m, 5H).

後処理

  1. washwashed with an aqueous solution of HCl (2 M)
  2. customThe phases were separated by means of a phase separator column
  3. customthe solvent was removed by evaporation

出典と根拠

ORDレコード
ord-184d37613b5044d58a5e7709fb514b39
出典データセット
uspto-grants-2012_01
特許番号
US08106208B2

反応ノート

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