N-Benzyl trans-4,5-bis(hydroxymethyl)isoxazolidine → (+/-)-3-[(Benzylamino)methyl]butane-1,2,4-triol

HRID 533215Notes

Reaction equation

HRID 533215 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([CH2:13][OH:14])[C@H:10]([CH2:15][OH:16])[O:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Zn]>[CH2:1]([NH:8][CH2:12][CH:11]([CH2:13][OH:14])[CH:10]([OH:9])[CH2:15][OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86653881N-Benzyl trans-4,5-bis(hydroxymethyl)isoxazolidine

Product 1

HCID 67024107(+/-)-3-[(Benzylamino)methyl]butane-1,2,4-triol

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc dust (0.47 g, 7.2 mmol) was added to a solution of N-benzyl trans-4,5-bis(hydroxymethyl)isoxazolidine (0.32 g, 1.43 mmol) in acetic acid (6 ml) and the mixture stirred vigorously for 1.5 hrs after which time the starting material had been consumed. The mixture was filtered through a plug of celite and the filtrate concentrated to dryness before being redissolved in DCM, preabsorbed onto silica and then fractionated by chromatography, eluting isocratically with M/7M NH3-MeOH, (4:1) to give the aminotriol (0.26 g, 81%) as an immobile syrup. 1H NMR (CDCl3) δ 3.90 (q, J=4.0 Hz, 1H), 3.80 (s, 2H), 3.75 (d, J=5.1 Hz, 2H), 3.66 (dq, J=11.7, 3.9 Hz, 2H), 2.94 (d, J=6.9 Hz, 2H), 1.78 (m, 1H). 13C NMR 138.9, 129.1, 128.7, 127.9, 73.7, 65.4, 65.3, 54.4, 48.9, 43.9. −ESMS—clean spectrum shows only MH+ (226) and MNa+ (248), C12H19NO3.

Workup

  1. customhad been consumed
  2. filtrationThe mixture was filtered through a plug of celite
  3. concentrationthe filtrate concentrated to dryness
  4. dissolutionbefore being redissolved in DCM
  5. custompreabsorbed onto silica
  6. washeluting isocratically with M/7M NH3-MeOH, (4:1)
  7. customto give the aminotriol (0.26 g, 81%) as an immobile syrup

Sources & evidence

ORD record
ord-7508340c80f943adb690719cedbda831
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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