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

HRID 1444714ノート

反応式

HRID 1444714 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4b672c3a030b4ecbb290c49910330133
出典データセット
uspto-grants-2010_02
特許番号
US07662811B2

反応ノート

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