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

HRID 2093448노트

반응식

HRID 2093448 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9375b95bbb6845b08e269fbbf7d66f7c
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445495B2

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