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

HRID 1377701Notes

Reaction equation

HRID 1377701 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])[OH:3].[C:11]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH:21]1[CH2:22][CH2:23][N:18]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:19][CH2:20]1)[OH:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1120582-Amino-alpha-methylbenzenemethanolHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 57248020methyl-(2-(1-Boc-4-piperidinylamino)phenyl) carbinol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl-2-aminophenyl carbinol from Step 1 above (0.86 g, 6.3 mmol), N-Boc-4-piperidone (2.5 g, 12.6 mmol), and acetic acid (1.08 mL, 1.13 g, 18.9 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 18 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 methyl-(2-(1-Boc-4-piperidinylamino)phenyl) carbinol.

Workup

  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

Sources & evidence

ORD record
ord-643bf4d9730c49f99260a57759e22143
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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