Formaldehyde → 4-(t-Butoxycarbonyl)-1-methylpiperazine-2-carboxamide

HRID 874967ノート

反応式

HRID 874967 の反応式
[C:1]([CH:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)(=[O:3])[NH2:2].C=O.[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[C:1]([CH:4]1[N:9]([CH3:19])[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)(=[O:3])[NH2:2]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11042527Tert-butyl 3-carbamoylpiperazine-1-carboxylate

生成物 1

HCID 231459204-(t-Butoxycarbonyl)-1-methylpiperazine-2-carboxamide収率 86.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

tert-Butyl 3-carbamoylpiperazine-1-carboxylate (340 mg, 1.48 mmol) was dissolved in methanol (10 mL) and cooled to 0° C. To the reaction mixture were added 35% formaline solution (185 mg) followed by sodium triacetoxyborohydride (0.95 g, 4.48 mmol). The reaction mixture was allowed to warm up to room temperature and further stirred for 4 h. The reaction mixture was quenched with 10% NaHCO3 solution. The reaction mixture was diluted with EtOAc and the organic layer was separated in separatory funnel. The organic layer was dried over anhydrous Na2SO4 and concentrated in reduced pressure to afford tert-butyl 3-carbamoyl-4-methylpiperazine-1-carboxylate (310 mg, yield 86%). 1H NMR (300 MHz, CDCl3) δ 6.51 (br s, 1H), 5.47 (br s, 1H), 4.21-4.15 (m, 1H), 4.03-3.97 (m, 1H), 2.93-2.81 (m, 3H), 2.64-2.59 (dd, J=10.6 Hz, 3.8 Hz, 1H), 2.31 (s, 3H), 2.24-2.19 (td, J=11.7 Hz, 3.3 Hz, 1H), 1.46 (s, 9H). MS (ESI) m/z: Calculated for C11H21N3O3: 243.16. found: 244.3 (M+H)+

後処理

  1. temperatureto warm up to room temperature
  2. customThe reaction mixture was quenched with 10% NaHCO3 solution
  3. additionThe reaction mixture was diluted with EtOAc
  4. customthe organic layer was separated in separatory funnel
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated in reduced pressure

出典と根拠

ORDレコード
ord-848205728a0b4f09b22f3a26c1328d7d
出典データセット
uspto-grants-2015_03
特許番号
US08981084B2

反応ノート

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