Di-tert-butyl dicarbonate → Tert-Butyl (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylcarbamate

HRID 132803Notes

Reaction equation

HRID 132803 reaction equation
[NH2:1][CH2:2][C@@H:3]([C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[O:6]1)[OH:4].[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O>C1COCC1>[CH3:10][C:7]1([CH3:11])[O:6][C@@H:5]([C@@H:3]([OH:4])[CH2:2][NH:1][C:13](=[O:12])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][O:8]1

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 59734745(1S)-2-amino-1-[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

Product 1

HCID 14249481Tert-Butyl (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-hydroxyethylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aminoalcohol 23 was dissolved in THF and BOC2O was added and stirred for several hrs. The solvent was removed and the product purified using silica gel chromatography.

Workup

  1. customThe solvent was removed
  2. customthe product purified

Sources & evidence

ORD record
ord-6dacd23111d34dacac13d12d18d78972
Source dataset
uspto-grants-2008_06
Patent number
US07388118B2

Reaction notes

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