Water → HCID 22882486, compound

HRID 451869Notes

Reaction equation

HRID 451869 reaction equation
C[O:2][C:3](=O)[C:4]([CH3:21])([CH3:20])[CH2:5][C@H:6]1[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[OH:2][CH2:3][C:4]([CH3:21])([CH3:20])[CH2:5][C@H:6]1[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[N:7]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22882590HCID 22882590, compound

Product 1

HCID 22882486HCID 22882486, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl 4-(3-methoxy-2,2-dimethyl-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (7 g, 22.21 mol) in THF was added with LiAlH4 (1.27 g, 33.31 mol). The reaction mixture was stirred overnight at rt. Water was added and extracted with EtOAc, dried over Na2SO4 and concentrated in vacuo to give the crude product (S)-tert-butyl 4-(3-hydroxy-2,2-dimethylpropyl)-2,2-dimethyloxazolidine-3-carboxylate (6.6 g, 100%) as an oil that was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 3.69 (m, 4H), 3.32 (m, 1H), 1.82 (m, 1H), 1.54 (s, 3H), 1.48 (s, 9H), 1.42 (s, 3H), 1.22 (m, 1H), 0.91 (m, 3H), 0.72 (s, 2H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1058aff0d0e242ba8ec17e552ac72057
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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