Benzaldehyde → (2S,5R)-1-allyl-4-benzyl-2,5-dimethylpiperazine

HRID 1057394

반응식

HRID 1057394 반응식
C(O)(=O)[C:2]1([CH2:12][CH2:11][CH:7]([C:8](O)=O)[C:4]1([CH3:6])C)C.[CH2:15]([N:18]1[CH2:23][C@@H:22]([CH3:24])[NH:21][CH2:20][C@@H:19]1[CH3:25])[CH:16]=[CH2:17].C(=O)C1C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(O)(=O)C>[CH2:15]([N:18]1[CH2:23][C@@H:22]([CH3:24])[N:21]([CH2:8][C:7]2[CH:4]=[CH:6][CH:2]=[CH:12][CH:11]=2)[CH2:20][C@@H:19]1[CH3:25])[CH:16]=[CH2:17]

참가 물질

7

반응물 4

HCID 240BenzaldehydeHCID 214911,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acidHCID 5049666Sodium triacetoxyborohydrideHCID 11291191(2S,5R)-1-allyl-2,5-dimethylpiperazine

생성물 1

HCID 12017828(2S,5R)-1-allyl-4-benzyl-2,5-dimethylpiperazine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of the camphoric acid salt of (+)-(2S,5R)-1-allyl-2,5-dimethylpiperazine from Preparation 1 (78.2 g) and benzaldehyde (26.5 g) in tetrahydrofuran (500 ml) containing glacial acetic acid (2 ml) was added sodium triacetoxyborohydride (93.3 g) portionwise over 10 minutes. The resulting mixture was stirred at room temperature for 4 hours. The reaction was partitioned between ethyl acetate (1500 ml) and aqueous sodium hydroxide (750 ml of 2N solution). The layers were separated and the organic phase was washed with 10% sodium metabisulphite solution (200 ml) and saturated brine solution. The organic layer was dried (MgSO4) and evaporated to dryness in vacuo to give the title compound, 52.1 g.

후처리

  1. customThe reaction was partitioned between ethyl acetate (1500 ml) and aqueous sodium hydroxide (750 ml of 2N solution)
  2. customThe layers were separated
  3. washthe organic phase was washed with 10% sodium metabisulphite solution (200 ml) and saturated brine solution
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated to dryness in vacuo

출처 및 근거

ORD 기록
ord-ec3e957b2f1a43799f6134670053e092
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514975B1

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