Trifluoroacetic acid → HCID 57667108, compound

HRID 600842Notes

Reaction equation

HRID 600842 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[CH:25](OC)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.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]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[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 62375Benzaldehyde dimethyl acetalHCID 5049666Sodium triacetoxyborohydrideHCID 57667036HCID 57667036, compound

Product 1

HCID 57667108HCID 57667108, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred solution of (S)-2,2-dimethyl-4-phenylaminomethyl-oxazolidine-3-carboxylic acid tert-butyl ester (495 mg; example 2.a) at r.t. in 1,2-dichloroethane (10 ml) under an argon atmosphere were added benzaldehyde dimethyl acetal (0.37 ml), trifluoroacetic acid (0.13 ml) and sodium triacetoxyborohydride (571 mg). The mixture was stirred at room temperature overnight. The mixture was directly adsorbed on silica gel and purified by chromatography (SiO2; gradient:heptane->heptane/EtOAc 7:3) to give (S)-4-[(benzyl-phenyl-amino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (492 mg, 77%) as a colourless viscous oil. MS (ISP): 397.4 ([M+H]+)

Workup

  1. custompurified by chromatography (SiO2; gradient:heptane->heptane/EtOAc 7:3)

Sources & evidence

ORD record
ord-f7fbe9662ad94f959c7f2301db999dbe
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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