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

HRID 2414033Notes

Reaction equation

HRID 2414033 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 (5B, 22.1 g, 0.146 mol) in 95% EtOH (150 mL) was added glacial acetic acid (25 mL) and 10% Pd/C (MCB, 2.0 g). The reduction was carried out in a Parr apparatus at 50 psi of H2 during a 48 h period at RT. The catalyst was removed by filtration through a Millipore® filter, and the solvent removed under vacuum (2 days). The viscous, colorless syrup was dissolved in abs. EtOH (30 mL). Dilution with abs. Et2O (300 mL) gave a cloudy liquid which was placed in a refrigerator for two days. During this time, colorless crystals formed. They were washed with Et2O and dried in a vacuum oven at RT for two days. The yield of (+-)(2R*,3R*)-2-amino-methyl-1,3-butanediol acetate was 25.6 g (97%) mp 117°-121°, (C, H, N).

Workup

  1. customThe catalyst was removed by filtration through a Millipore®
  2. filtrationfilter
  3. customthe solvent removed under vacuum (2 days)
  4. dissolutionThe viscous, colorless syrup was dissolved in abs
  5. customEt2O (300 mL) gave a cloudy liquid which
  6. waitwas placed in a refrigerator for two days
  7. customDuring this time, colorless crystals formed
  8. washThey were washed with Et2O
  9. customdried in a vacuum oven at RT for two days

Sources & evidence

ORD record
ord-0bc9c9dd4a3c42c59e25759ac316451b
Source dataset
uspto-grants-1988_01
Patent number
US04720587

Reaction notes

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