Acetic Acid → (+-)(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate

HRID 1639152Notes

Reaction equation

HRID 1639152 reaction equation
[CH3:1][C@:2]([N+:8]([O-])=O)([C@H:5]([OH:7])[CH3:6])[CH2:3][OH:4].[C:11]([OH:14])(=[O:13])[CH3:12]>CCO.[Pd]>[C:11]([OH:14])(=[O:13])[CH3:12].[NH2:8][C@@:2]([CH3:1])([C@H:5]([OH:7])[CH3:6])[CH2:3][OH:4]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 13375425(+-)(2R*,3R*)-2-Methyl-2-nitro-1,3-butanediol

Product 1

HCID 86741969(+-)(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (±)-(2R*,3R*)-2-methyl-2-nitro-1,3-butanediol (11B, 13.93 g, 0.093 mol) in 95% EtOH (120 mL) was added glacial acetic acid (17 mL) and 10% Pd/C (MCB, 1.0 g). The mixture was reduced in a Parr apparatus at 50 psi of H2 for 48 h. The catalyst was then removed by filtration on a Celite® pad and the solvent removed to give the crude amine salt. Three portions of PhCH3 (50 mL) were added to the flask and removed by rotary evaporation to remove final traces of H2O and acetic acid. The residue, a viscous oil gradually solidified under high vacuum. The solid was triturated with Et2O, filtered and the resulting solid further washed with Et2O to give after drying, 16.23 g (97%) of (±)-(2R*3R*)-2-amino-2-methyl-1,3-butanediol acetate, mp 117°-121°, (C,H,N).

Workup

  1. customThe catalyst was then removed by filtration on a Celite® pad
  2. customthe solvent removed

Sources & evidence

ORD record
ord-a0bb670d4d33418c8a354cbbc0919482
Source dataset
uspto-grants-1989_11
Patent number
US04882358

Reaction notes

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