tert-Butyl 4(S)-(2(S)-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate → tert-Butyl 4(S)-(2(S)-hydroxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 507834Notes

Reaction equation

HRID 507834 reaction equation
C([O:8][CH2:9][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H: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][C@H:10]([CH:26]([CH3:28])[CH3:27])[CH2:11][C@H: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 68624760tert-Butyl 4(S)-(2(S)-benzyloxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Product 1

HCID 68624386tert-Butyl 4(S)-(2(S)-hydroxymethyl-3-methylbutyl)-2,2-dimethyloxazolidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.58 g of tert-butyl 4(S)-(2(S)-benzyloxymethyl-3-methylbutyl)-2,2-dimethyl-oxazolidine-3-carboxylate in 100 ml of tetrahydrofuran is hydrogenated at room temperature in the presence of 0.720 g of 10% Pd/C over 1 hour. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a yellowish oil. Rf=0.28 (1:2 EtOAc-heptane); Rt=4.48 (gradient I).

Workup

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

Sources & evidence

ORD record
ord-2dc9735e8586411a8123c7f5dc58fe64
Source dataset
uspto-grants-2010_08
Patent number
US07786307B2

Reaction notes

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