Aniline → (RS)-2,2,4-trimethyl-4-phenylaminomethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 600849Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:12]([CH:14]=O)([CH3:13])[CH2:11][O:10][C:9]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:13])([CH2:14][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of (RS)-4-formyl-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (300 mg) at r.t. in methanol (3 ml) was added aniline (132 mg) and the mixture was heated at 80° C. for 3 h. NaBH4 (93 mg) was then added and the mixture was stirred at 60° C. for 16 h, then cooled to r.t. and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient:heptane/ethyl acetate) to give (RS)-2,2,4-trimethyl-4-phenylaminomethyl-oxazolidine-3-carboxylic acid tert-butyl ester (181 mg, 46%) as a yellow oil. MS (ISP): 321.1 ([M+H]+).

Workup

temperaturecooled to r.t.
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2; gradient:heptane/ethyl acetate)

Sources & evidence

ORD record: ord-243d595306e541fea2587a2baec93682
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902238B2

Reaction notes

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