Tert-butyl 4-(2-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate → Tert-butyl 4-(2-hydroxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 252403Notes

Reaction equation

HRID 252403 reaction equation
C([O:8][CH2:9][CH:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][CH:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])C1C=CC=CC=1>O1CCCC1.[Pd]>[OH:8][CH2:9][CH:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][CH:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[N:13]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

4

Reactant 1

HCID 66887921Tert-butyl 4-(2-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 66888909Tert-butyl 4-(2-hydroxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.40 g of tert-butyl 4-(2-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate in 450 ml of tetrahydrofuran is hydrogenated at room temperature in the presence of 3.07 g of 10% Pd/C over 2 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.28 (1:2 EtOAc-heptane). Rt=4.58 (gradient I).

Workup

  1. filtrationThe reaction mixture is clarified by filtration
  2. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-4656f0d8f9b841c8828e90faff7ab2c9
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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