(R)-benzyl 2-methylpiperazine-1-carboxylate → (R)-benzyl 4-(3-amino-2-fluorobenzyl)-2-methylpiperazine-1-carboxylate

HRID 539720ノート

反応式

HRID 539720 の反応式
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[NH2:18][C:19]1[C:20]([F:27])=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O>C1COCC1>[NH2:18][C:19]1[C:20]([F:27])=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][N:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C@H:2]([CH3:1])[CH2:7]1

参加物

4

反応物 2

HCID 40424346(R)-benzyl 2-methylpiperazine-1-carboxylateHCID 552821973-Amino-2-fluorobenzaldehyde

生成物 1

HCID 58919233(R)-benzyl 4-(3-amino-2-fluorobenzyl)-2-methylpiperazine-1-carboxylate収率 108.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a room temperature solution of (R)-benzyl 2-methylpiperazine-1-carboxylate (1.7 g, 7.2 mmol, 1.0 equiv) and 3-amino-2-fluorobenzaldehyde (1.0 g, 7.2 mmol, 1.0 equiv) in THF (10 mL) was added NaHB(OAc)3 (3.84 g, 18.1 mmol, 2.5 equiv) as a solid in one portion. After stirring at room temperature for 1.5 h, the reaction was complete, as determined by LCMS. The remaining reducing reagent was quenched by the careful addition of aq. satd. NaHCO3, and the mixture was diluted with EtOAc. The layers were separated and the organic layer was washed with aq. satd. NaHCO3 and brine, dried over sodium sulfate and concentrated in vacuo to provide (R)-benzyl 4-(3-amino-2-fluorobenzyl)-2-methylpiperazine-1-carboxylate (2.8 g, >100% mass recovery). The material was used without further purification. LCMS m/z (APCI)=358.5 (M+H).

後処理

  1. customwas quenched by the careful addition of aq. satd
  2. additionNaHCO3, and the mixture was diluted with EtOAc
  3. customThe layers were separated
  4. washthe organic layer was washed with aq. satd
  5. dry with materialNaHCO3 and brine, dried over sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f337ae41161f404ab11a9c13d2009ced
出典データセット
uspto-grants-2014_10
特許番号
US08871768B2

反応ノート

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