Aluminium lithium hydride → (R)-N-methyl-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine

HRID 1444714노트

반응식

HRID 1444714 반응식
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[C@H:14]([NH:18][C:19](=O)OC(C)(C)C)[CH2:13][CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1(C)C=CC=CC=1>[CH3:19][NH:18][C@H:14]1[C:15]2[C:10](=[CH:9][C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:17][CH:16]=2)[CH2:11][CH2:12][CH2:13]1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 56594897(R)-tert-butyl 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

생성물 1

HCID 68679772(R)-N-methyl-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

In 50 mL of dry toluene, 2.0 g (5.8 mmol) of (R)-tert-butyl 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate and 1.5 g (41 mmol) of lithium aluminum hydride were combined and gently refluxed for 24 h. Next the mix was quenched with 5 g of sodium sulfate decahydrate and allowed to stir for 2 h. The mix was then filtered over celite and the pad was washed with ethyl acetate several times. The filtrate was then concentrated and the crude was purified on silica using 0 to 5% MeOH (10% ammonium hydroxide) in ethyl acetate to give the product. MS 259 (ESI, pos. ion).

후처리

  1. temperaturegently refluxed for 24 h
  2. customNext the mix was quenched with 5 g of sodium sulfate decahydrate
  3. filtrationThe mix was then filtered over celite
  4. washthe pad was washed with ethyl acetate several times
  5. concentrationThe filtrate was then concentrated
  6. customthe crude was purified on silica using 0 to 5% MeOH (10% ammonium hydroxide) in ethyl acetate
  7. customto give the product

출처 및 근거

ORD 기록
ord-4b672c3a030b4ecbb290c49910330133
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662811B2

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