Isobutylamine → HCID 86617383, compound

HRID 1435147Notes

Reaction equation

HRID 1435147 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([NH2:19])[CH:16]([CH3:18])[CH3:17].[C:20]([O:24][C:25]([N:27]1[CH2:33][CH2:32][CH2:31][C@H:28]1[CH:29]=O)=[O:26])([CH3:23])([CH3:22])[CH3:21].[OH-].[Na+]>ClCCCl.O>[CH2:15]([NH:19][CH2:29][C@@H:28]1[CH2:31][CH2:32][CH2:33][N:27]1[C:25]([O:24][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:26])[CH:16]([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 6558IsobutylamineHCID 14798Sodium HydroxideHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86617383HCID 86617383, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

Sodium triacetoxyborohydride (2.9 g, 14 mmol, 1.4 eq) is added to a solution of isobutylamine (0.77 g, 10 mmol, 1.05 eq) and N-(tert-butoxycarbonyl)-L-prolinal (2 g, 10 mmol, 1 eq) in 1,2-dichloroethane (35 ml). After 1 hr water (25 ml) followed by 2N aqueous sodium hydroxide (25 ml) is added. The aqueous layer is separated and extracted with dichloromethane (3×50 ml). The organic layers are combined and dried over magnesium sulphate, filtered, and concentrated in vacuo giving a residue. The residue is purified by flash chromatography, eluting with 20-70% methanol in ethyl acetate to give the tert-butyl (2S)-2-[(isobutylamino)methyl]pyrrolidine-1-carboxylate (1.95 g, 76%): 1H NMR (300 MHz, CDCl3) δH: 3.69-4.07 (1H, m), 3.19-3.50 (2H, m), 2.67-2.87 (1H, m), 2.48-2.65 (1H, m), 2.35-2.47 (2H, m), 1.62-2.01 (5H, m), 1.34-1.53 (9H, m) and 0.88 (6H, d); LCMS: Rt=2.74 (6 min method) [M+H]=257.5.

Workup

  1. additionis added
  2. customThe aqueous layer is separated
  3. extractionextracted with dichloromethane (3×50 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customgiving a residue
  8. customThe residue is purified by flash chromatography
  9. washeluting with 20-70% methanol in ethyl acetate

Sources & evidence

ORD record
ord-c3fd264fb9524557b2600ef1d9161465
Source dataset
uspto-grants-2009_11
Patent number
US07615648B2

Reaction notes

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