3-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylate → (S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1917497Notes

Reaction equation

HRID 1917497 reaction equation
[CH3:1][C:2]1([CH3:18])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([C:14](OC)=[O:15])[CH2:4][O:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[OH:15][CH2:14][C@H:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:18])[N:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 6882203-tert-butyl 4-methyl (4R)-2,2-dimethyl-1,3-oxazolidine-3,4-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11053463(S)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterYield 62.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (R)-3-tert-butyl 4-methyl 2,2-dimethyloxazolidine-3,4-dicarboxylate (5 g, 19.3 mmol) in anhydrous diethyl ether was chilled in an ice bath and 1 M LiAlH4 in diethyl ether (38 mL, 38.6 mmol) was added dropwise under an N2 atmosphere. The reaction was allowed to warm to room temperature with stirring overnight. The reaction was quenched by slowly adding saturated aqueous Na2SO4 (5 mL). The slurry was filtered through a pad of Celite. The Celite pad was rinsed with EtOAc and the solution was dried in vacuo to yield (S)-tert-butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate (2.77 g, 12 mmol) as a clear oil. [M+H] calc'd for C11H21NO4, 232; found, 232.

Workup

  1. customThe reaction was quenched by slowly adding saturated aqueous Na2SO4 (5 mL)
  2. filtrationThe slurry was filtered through a pad of Celite
  3. washThe Celite pad was rinsed with EtOAc
  4. customthe solution was dried in vacuo

Sources & evidence

ORD record
ord-280c6754af5c4bf58e471eef1a7d2959
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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