Trifluoroacetic acid → HCID 57667096, compound

HRID 600835Notes

Reaction equation

HRID 600835 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].CO[C:25]([CH3:27])=[CH2:26].FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][N:14]([CH:25]([CH3:27])[CH3:26])[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 4

HCID 6422Trifluoroacetic acidHCID 83002-MethoxypropeneHCID 5049666Sodium triacetoxyborohydrideHCID 57667036HCID 57667036, compound

Product 1

HCID 57667096HCID 57667096, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of (S)-2,2-dimethyl-4-phenylaminomethyl-oxazolidine-3-carboxylic acid tert-butyl ester (650 mg) at r.t. in 1,2-dichloroethane (15 ml) under an argon atmosphere were added 2-methoxypropene (0.30 ml), trifluoroacetic acid (0.16 ml) and sodium triacetoxyborohydride (674 mg). The mixture was heated to 40° C. overnight. The mixture was cooled to r.t., directly adsorbed on silica gel and purified by chromatography (SiO2; gradient:cyclohexane->cyclohexane/EtOAc 7:3) to give (S)-4-[(isopropyl-phenyl-amino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (659 mg, 89%) as light yellow viscous oil. MS (ISP): 349.5 ([M+H]+)

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. custompurified by chromatography (SiO2; gradient:cyclohexane->cyclohexane/EtOAc 7:3)

Sources & evidence

ORD record
ord-32363e059c7a4a23adf6d054826c7c0a
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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