Acetaldehyde → HCID 57667084, compound

HRID 600832Notes

Reaction equation

HRID 600832 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23](=O)[CH3:24].[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][N:14]([CH2:23][CH3:24])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:22])[CH3:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57667054HCID 57667054, compound

Product 1

HCID 57667084HCID 57667084, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of (R)-2,2-dimethyl-4-phenylaminomethyl-oxazolidine-3-carboxylic acid tert-butyl ester (730 mg) at r.t. in methanol (20 ml) under an argon atmosphere were added acetaldehyde (0.67 ml), ZnCl2 (1.30 g) and NaBH3CN (0.45 g). The mixture was warmed to 40° C. and stirring at that temperature was continued for 17 h. The mixture was cooled to r.t., directly adsorbed on silica gel and purified by column chromatography (SiO2; gradient:cyclohexane->cyclohexane/EtOAc 4:1) to give (R)-4-[(ethyl-phenyl-amino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (614 mg, 77%) as colorless viscous oil. MS (ISP): 335.5 ([M+H]+)

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. custompurified by column chromatography (SiO2; gradient:cyclohexane->cyclohexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-2e97473f6c3d4fc2be342cf3864230b8
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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