Acetic Acid → HCID 22914698, compound

HRID 1377704Notes

Reaction equation

HRID 1377704 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH2:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][OH:23].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:19][C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[CH2:22][OH:23])[CH:10]([C:15]([O:17][CH3:18])=[O:16])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 214392-Aminobenzyl alcoholHCID 5003444Sodium cyanoborohydrideHCID 112768931-tert-Butyl 3-methyl 4-oxopiperidine-1,3-dicarboxylate

Product 1

HCID 22914698HCID 22914698, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-Boc-4-oxo-3-piperidinecarboxylate from Step 1 above (3.86 g, 15 mmol) was combined with 2-aminobenzyl alcohol (1.5 g, 12.2 mmol) and acetic acid (1.29 mL, 1.35 g, 22.5 mmol) in methanol (10 mL). Sodium cyanoborohydride (0.94 g, 15 mmol) was added and the mixture was stirred at ambient temperature for 3.5 h. The solvent was removed in vacuo and the residue treated with ethyl acetate (100 mL). The solution was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was chromatographed on silica gel eluted with 1:4, 1:2, and 3:5 EtOAc:hexane. The combined product fractions were evaporated to dryness in vacuo to give methyl 1-Boc-4-(2-hydroxymethylphenylamino)-3-piperidine carboxylate.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue treated with ethyl acetate (100 mL)
  3. washThe solution was washed with saturated aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washeluted with 1:4, 1:2, and 3:5 EtOAc
  9. customThe combined product fractions were evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-bfad65b9b7e44f9290ac36d8f8e90fb4
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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