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

HRID 1377697

반응식

HRID 1377697 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-739770d9196e453ca2ce9b4ac7dc3405
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665719

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