Methylamine → tert-butyl (S)-3-cyclopentyl-1-(methylamino)propan-2-ylcarbamate

HRID 2355463Notes

Reaction equation

HRID 2355463 reaction equation
[CH:1]1([CH2:6][C@H:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:8]OS(C)(=O)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22][NH2:23]>>[CH:1]1([CH2:6][C@H:7]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:8][NH:23][CH3:22])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 59383009(S)-2-(tert-butoxycarbonylamino)-3-cyclopentylpropyl methanesulfonate

Product 1

HCID 59383030tert-butyl (S)-3-cyclopentyl-1-(methylamino)propan-2-ylcarbamateYield 43%

Procedure

A mixture of crude tert-butyl (S)-3-cyclopentyl-1-(methanesulfonyloxy)propan-2-ylcarbamate in ethanolic methylamine (30 mL) was heated under reflux overnight. The solvent was removed in vacuo and the residue was purified by silica chromatography to obtain tert-butyl (S)-3-cyclopentyl-1-(methylamino)propan-2-ylcarbamate (900 mg, 43% for 3 steps from) as a solid (900 mg, yield 43% for 3 steps from tert-butyl (S)-3-cyclopentyl-1-(t-butyldimethylsilyloxy)propan-2-ylcarbamate). 1H NMR (CDCl3, 400 MHz) δ 1.10 (m, 2H), 1.44 (s, 9H), 1.49 (m, 3H), 1.60 (m, 3H), 1.81 (m, 3H), 2.69 (s, 3H), 2.90 (m, 1H), 3.17 (m, 1H), 3.92 (brs, 1H), 5.66 (brs, 1H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-56a42de46f4b405cabc0138c7f14bbdd
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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