Mono-tert-butyl carbonate → 3-(t-Butoxycarbonylamino)-1-benzyl-4-methylpyrrolidine

HRID 1722290Notes

Reaction equation

HRID 1722290 reaction equation
[NH2:1][CH:2]1[CH:6]([CH3:7])[CH2:5][N:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.[C:15]([O:19][C:20](O)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CO>[C:15]([O:19][C:20]([NH:1][CH:2]1[CH:6]([CH3:7])[CH2:5][N:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 3015642Mono-tert-butyl carbonateHCID 142112411-Benzyl-4-methylpyrrolidin-3-amine

Product 1

HCID 139331343-(t-Butoxycarbonylamino)-1-benzyl-4-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-amino-1-benzyl-4-methylpyrrolidine (9.5 g) in methanol (190 ml) is added anhydrous t-butoxycarboxylic acid (13.0 g) at room temperature, and the mixture is stirred for one hour. Methanol is distilled off under reduced pressure, and to the resulting residue is added water. The mixture is extracted with dichloromethane, and the extract is dried over magnesium sulfate and then dichloromethane is distilled off. The residue is purified by silica gel column chromatography (solvent, dichloromethane:methanol=19:1) to give 3-(t-butoxycarbonylamino)-1-benzyl-4-methylpyrrolidine (isomer A) (4.4 g), as colorless prisms, m.p. 131.5°-132.7° C.

Workup

  1. distillationMethanol is distilled off under reduced pressure
  2. additionto the resulting residue is added water
  3. extractionThe mixture is extracted with dichloromethane
  4. dry with materialthe extract is dried over magnesium sulfate
  5. distillationdichloromethane is distilled off
  6. customThe residue is purified by silica gel column chromatography (solvent, dichloromethane:methanol=19:1)

Sources & evidence

ORD record
ord-d9a39b3f667847d9b3f106fd44198c6f
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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