Water → Benzyl [4-(5-methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate

HRID 518805ノート

反応式

HRID 518805 の反応式
[BH4-].[Na+].[I-].[CH2:4]([O:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][N+:24]([CH3:27])=[CH:23][C:22]=2[O:28][CH3:29])=[CH:17][C:16]=1[O:30][CH:31]([CH3:33])[CH3:32])=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.C(=O)(O)[O-].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:29][O:28][C:22]1[CH2:23][N:24]([CH3:27])[CH2:25][CH2:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12](=[O:13])[O:11][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[C:16]([O:30][CH:31]([CH3:33])[CH3:32])[CH:17]=1

参加物

7

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 866979754-[4-{[(Benzyloxy)carbonyl]amino}-3-(propan-2-yloxy)phenyl]-3-methoxy-1-methylpyridinium iodide

生成物 1

HCID 86697977Benzyl [4-(5-methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate収率 53.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

486 mg of NaBH4 are added, in portions, to a suspension of 4.57 g of 4-[4-{[(benzyloxy)carbonyl]amino}-3-(propan-2-yloxy)phenyl]-3-methoxy-1-methylpyridinium iodide in 100 ml of ethanol brought to 5° C. The reaction medium is stirred for 1 h 30 at ambient temperature. 50 ml of water, 50 ml of a saturated aqueous sodium bicarbonate solution and 100 ml of ethyl acetate are added. The two phases are separated, and the aqueous phase is washed with twice 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a mixture of dichloromethane and (MeOH+10% NH4OH) (99/1 to 90/10). 1.87 g of benzyl [4-(5-methoxy-1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-(propan-2-yloxy)phenyl]carbamate are obtained in the form of an orangey-coloured oil.

後処理

  1. custombrought to 5° C
  2. customThe two phases are separated
  3. washthe aqueous phase is washed with twice 50 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification
  8. washis carried out by flash chromatography on silica gel (40-63 μm), elution
  9. additionbeing carried out with a mixture of dichloromethane and (MeOH+10% NH4OH) (99/1 to 90/10)

出典と根拠

ORDレコード
ord-066d47a5843142f4abec23566e5218ba
出典データセット
uspto-grants-2015_08
特許番号
US09115140B2

反応ノート

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