Acetic Acid → phenyl-(2-(1-Boc-4-piperidinylamino)phenyl) carbinol

HRID 1377697

反応式

HRID 1377697 の反応式
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:16]([N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:5]1([CH:4]([C:3]2[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=2[NH:1][CH:26]2[CH2:27][CH2:28][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:24][CH2:25]2)[OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 2708102-AminobenzhydrolHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 57083091phenyl-(2-(1-Boc-4-piperidinylamino)phenyl) carbinol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

2-Aminobenzhydrol from Step 1 above (1.0 g, 5 mmol), N-Boc-4-piperidone (2.0 g, 10 mmol), and acetic acid (0.86 mL, 0.9 g, 15 mmol) were combined in methanol (10 mL). Sodium cyanoborohydride (0.79 g, 12.5 mmol) was added in portions, and the mixture was stirred at ambient temperature for 42 hours. The mixture was concentrated in vacuo. Ethyl acetate (100 mL) was added to the residue and the resulting mixture was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and evaporated in vacuo. The residue was chromatographed on silica gel eluted with 1:9 then 15:85 EtOAc:hexane. The combined product fractions were evaporated to dryness in vacuo to give phenyl-(2-(1-Boc-4-piperidinylamino)phenyl) carbinol.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. additionEthyl acetate (100 mL) was added to the residue
  3. washthe resulting mixture was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluted with 1:9
  9. customThe combined product fractions were evaporated to dryness in vacuo

出典と根拠

ORDレコード
ord-739770d9196e453ca2ce9b4ac7dc3405
出典データセット
uspto-grants-1997_09
特許番号
US05665719

関連ノート

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