Sodium Hydroxide → HCID 86617384, compound

HRID 1435148Notes

Reaction equation

HRID 1435148 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.[CH2:11]([NH:15][CH2:16][C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:12]([CH3:14])[CH3:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl.CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5][N:15]([CH2:16][C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 357463,5-DichlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86617383HCID 86617383, compound

Product 1

HCID 86617384HCID 86617384, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-dichlorobenzaldehyde (0.79 g, 4.5 mmol, 3 eq) in 1,2-dichloroethane (2 ml) is added to a solution of tert-butyl (2S)-2-[(isobutylamino)methyl]pyrrolidine-1-carboxylate (0.38 g, 1.5 mmol, 1 eq) in 1,2-dichloroethane (8 ml) followed by a solution of sodium triacetoxyborohydride (0.95 g, 4.5 mmol, 3 eq) in DMF (2 ml). After 16 hrs water (5 ml) followed by 2N aqueous sodium hydroxide (5 ml) is added. The biphasic mixture is passed through a hydrophobic frit to separate the organic layer. Methanol is added to the organic layer and the solution is loaded onto a SCX-2 (10 g) column. The column is washed with methanol (50 ml) and then the basic material is eluted with 2M ammonia in methanol (50 ml). The solvent is removed in vacuo to give the tert-butyl (2S)-2-{[(3,5-dichlorobenzyl)(isobutyl)amino]methyl}pyrrolidine-1-carboxylate (0.61 g, 98%). LCMS: Rt=4.17 (6 min method) [M+H]=415.4.

Workup

  1. additionis added
  2. customto separate the organic layer
  3. additionMethanol is added to the organic layer
  4. washThe column is washed with methanol (50 ml)
  5. washthe basic material is eluted with 2M ammonia in methanol (50 ml)
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-3616c6c0298c48d8b43709753246af83
Source dataset
uspto-grants-2009_11
Patent number
US07615648B2

Reaction notes

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