Aluminium lithium hydride → 7-Hydroxymethyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine

HRID 1594584노트

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HRID 1594584 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH:11]1[CH2:27][N:14]2[CH2:15][CH2:16][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:18](=O)[CH:13]2[CH2:12]1)=O>C1COCC1>[OH:8][CH2:9][CH:11]1[CH2:27][N:14]2[CH2:15][CH2:16][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:18][CH:13]2[CH2:12]1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 217064047-Methoxycarbonyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-1-one

생성물 1

HCID 217063797-Hydroxymethyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine수율 89.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

A suspension of 3.20 g (84.3 mmol) of lithium aluminum hydride in 30 mL of dry THF was cooled to 0° C. and treated dropwise with a solution of 8.00 g (27.7 mmol) of 7-methoxycarbonyl-2-phenylmethyl-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazin-1-one (Jones, R. C. F., Howard, K. J., J. Chem. Soc., Perkin Trans. 1, 1993, 2391) in 80 mL of dry THF. After 30 min the reaction was carefully quenched with 3 mL of water, 3 mL of 15% NaOH and 9 of mL water. The mixture was filtered, the filtrate evaporated, the residue taken up in ethyl acetate and washed with brine. The organic layer was dried (magnesium sulfate), filtered, and evaporated to give 6.09 g (89%) of the title compound as a mixture of (7RS,8aSR)- and (7SR,8aSR)-isomers of sufficient purity for use in the next reaction (Preparation 2). m/z (MH+) 247.

후처리

  1. customAfter 30 min the reaction was carefully quenched with 3 mL of water, 3 mL of 15% NaOH and 9 of mL water
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. washwashed with brine
  5. dry with materialThe organic layer was dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-2383ba9519864116938382d102d8b539
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06284757B1

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