Sodium borohydride → Ethyl 1-(2-Aminoethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

HRID 1026448ノート

反応式

HRID 1026448 の反応式
[C:1]([CH2:3][N:4]1[C:12]2[CH2:11][C:10]([F:14])([F:13])[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:2].[BH4-].[Na+]>C(O)C>[NH2:2][CH2:1][CH2:3][N:4]1[C:12]2[CH2:11][C:10]([F:14])([F:13])[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 86683734Ethyl 1-(Cyanomethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

生成物 1

HCID 86683733Ethyl 1-(2-Aminoethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate収率 21%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Into a 100-mL round-bottom flask was placed a solution of 113m (3.3 g, 12.30 mmol, 1.00 equiv) in ethanol (30 mL) and NiCl2.6H2O (3.2 g, 13.45 mmol, 1.10 equiv), followed by the addition of NaBH4 (1.4 g, 37.01 mmol, 3.00 equiv) in several batches at 0° C. (FIG. 14). The resulting solution was stirred at room temperature for 24 h. The solids were filtered out and the filtrate was concentrated under vacuum. The resulting solution was diluted with 30 mL of ethyl acetate and washed with 1×30 mL of hydrogen chloride (2/V). The solution was adjusted to pH=9 with saturated aqueous sodium bicarbonate and extracted with 2×30 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 0.7 g (21%) of 113n as a light yellow oil.

後処理

  1. customInto a 100-mL round-bottom flask was placed
  2. filtrationThe solids were filtered out
  3. concentrationthe filtrate was concentrated under vacuum
  4. additionThe resulting solution was diluted with 30 mL of ethyl acetate
  5. washwashed with 1×30 mL of hydrogen chloride (2/V)
  6. extractionextracted with 2×30 mL of ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-4a4cd083d72b4f1a82ee445161c76372
出典データセット
uspto-grants-2014_05
特許番号
US08729072B2

反応ノート

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