Sodium Carbonate → (1S, 2S, 3R)-2,3-bis(hydroxymethyl)-1-cyclobutylamine

HRID 374264Notes

Reaction equation

HRID 374264 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:6]([CH2:7][OH:8])[CH2:5][C@H:4]1[NH2:9].CC(N(C1C=CC=CC=1)CC(O)=O)=O.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>>[OH:1][CH2:2][C@H:3]1[C@H:6]([CH2:7][OH:8])[CH2:5][C@@H:4]1[NH2:9]

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 131717654(1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine N-acetyl-L-phenylglycine

Product 1

HCID 55291246(1S, 2S, 3R)-2,3-bis(hydroxymethyl)-1-cyclobutylamine

Procedure

To the (1R, 2R, 3S)-2,3-bis(hydroxymethyl)-1-cyclobutylamine/N-acetyl-L-phenylglycine salt thus isolated is added an alkaline aqueous solution of, for example, sodium hydrogencarbonate, sodium carbonate or sodium hydroxide. Then the mixture is extracted with an organic solvent such as t-butanol or secbutanol. Or a solution of the salt is treated with an ion exchange resin. Then the salt is separated into the aimed free base (1R, 2R, 3S)-2,3-bis(hydromethyl)-1-cyclobutylamine and N-acetyl-L-phenylglycine. On the other hand, (1S, 2S, 3R)-2,3-bis(hydroxymethyl)-1-cyclobutylamine may be produced by the same method as the one described above except that the N-acetyl-L-phenylglycine is replaced by N-acetyl-D-phenylglycine.

Workup

  1. extractionThen the mixture is extracted with an organic solvent such as t-butanol or secbutanol
  2. additionOr a solution of the salt is treated with an ion exchange resin
  3. customThen the salt is separated into the aimed free base (1R, 2R, 3S)-2,3-bis(hydromethyl)-1-cyclobutylamine and N-acetyl-L-phenylglycine

Sources & evidence

ORD record
ord-b12c5dc7908249b7a75718137e6a3e54
Source dataset
uspto-grants-1992_11
Patent number
US05166397

Reaction notes

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