Benzylamine → HCID 57452747, compound

HRID 81112Notes

Reaction equation

HRID 81112 reaction equation
[CH:1]12[O:7][CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2]2.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[C:11]([O:10][C:8]([N:3]1[CH2:4][CH2:5][CH:6]([NH:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:1]([OH:7])[CH2:2]1)=[O:9])([CH3:14])([CH3:13])[CH3:12].[C:11]([O:10][C:8]([N:3]1[CH2:4][CH2:5][CH:6]([OH:7])[CH:1]([NH:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:2]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 21991116tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

Product 2

HCID 57452747HCID 57452747, compoundHCID 57452748HCID 57452748, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (500 g, 2.5 mol) in H2O (5 L) was added BnNH2 (294 g, 2.75 mol) at room temperature. The mixture was heated to reflux overnight. The mixture was extracted with DCM (1 L), dried over sodium sulfate, and concentrated under reduced pressure to give tert-butyl-4-(benzylamino)-3-hydroxypiperidine-1-carboxylate and tert-butyl-3-(benzylamino)-4-hydroxypiperidine-1-carboxylate, which were used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. extractionThe mixture was extracted with DCM (1 L)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b5e1451d7df4aa682a79677a4aa2a69
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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