tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamate → 1-(1-benzylpyrrolidin-3-yl)-N-methylmethanamine

HRID 1295870Notes

Reaction equation

HRID 1295870 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:12](=O)[NH:13][CH2:14][CH:15]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16]1)(C)(C)C>C1COCC1>[CH2:20]([N:17]1[CH2:18][CH2:19][CH:15]([CH2:14][NH:13][CH3:12])[CH2:16]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 5108694tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 46608321-(1-benzylpyrrolidin-3-yl)-N-methylmethanamineYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

To a cooled (−5° C.) and stirred solution of LAH (1 M, 7.6 ml) in dry THF (75 ml) was added a solution of (1-benzyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester (1.47 g, 5.06 mmol) in THF (22 ml) over 20 minutes. The mixture was then heated at reflux for 2.5 hrs and cooled to room temperature and quenched by successive addition of ethyl acetate (50 ml). The organic layer was then washed with water (2×), 10% NaOH and brine, dried and evaporated to give the desired product in 90% yield.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2.5 hrs
  3. temperaturecooled to room temperature
  4. customquenched by successive addition of ethyl acetate (50 ml)
  5. washThe organic layer was then washed with water (2×), 10% NaOH and brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-26bde80f474c4806bddca5de0ac9e020
Source dataset
uspto-grants-2007_07
Patent number
US07244758B2

Reaction notes

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