Hydrochloric Acid → Swainsonine

HRID 2082153Notes

Reaction equation

HRID 2082153 reaction equation
CC1(C)[O:13][C@@H:12]2[C@@H:4]([CH2:5][N:6]3[C@@H:11]2[C@H:10]([OH:14])[CH2:9][CH2:8][CH2:7]3)[O:3]1.Cl>C1COCC1>[CH2:8]1[CH2:7][N:6]2[C@@H:11]([C@H:12]([OH:13])[C@H:4]([OH:3])[CH2:5]2)[C@H:10]([OH:14])[CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 98591851,2-Isopropylidene Swainsonine

Product 1

HCID 51683SwainsonineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of swainsonine acetonide (104 mg, 0.49 mmol) in THF (6.5 ml) was added 6.0 ml of 6M HCl. The colorless solution was stirred overnight at room temperature. The solvent was removed in vacuo, leaving a colorless, viscous oil. The oil was then purified by an ion exchange chromatography (Dowex-1×8). Fractions (visualized with iodine or ninhydrin) were collected and concentrated in vacuo to furnish 68.5 mg(81% yield) of swainsonine as a white solid: mp and mixed mp 140-142 C; [α]D25 =-75.71 (c 2.33, MeOH); Rf=0.36 in 1-butanol:chloroform:ethanol:concentrated ammonium hydroxide (4:4:4:1); 1H NMR (D2O, ref. DSS, 300MHz) 4.34 (m, 1H, H-2), 4.24 (dd, J1,8a =3.7 Hz, J1,2 =6.1 Hz, 1H, H-1), 3.78 (dd, J=3.9, 9.3 & 10.7 Hz, 1H, H-8), 2.89 (m, 1H), 2.86 (dd, J=2.6 & 11.0 Hz, 1H, H-3), 2.53 (dd, J=7.8 & 11.0 Hz, 1H, H-3'), 2.04 (m, 1H), 1.96 (m, 1H), 1.89 (dd, J8a,8 =9.3 Hz, J8a,1 =3.7 Hz, H-8a), 1.70 (m, 1H), 1.49 (m, 1H), 1.22 (m, 1H); 13C NMR (D2O, ref: CH3CN, 100MHz) δ23.21, 32.51, 51.72, 60.65, 66.37, 69.08, 69.72, 72.87; HRMS(M+) 173.1052 calcd for C8H15NO3, found 173.1041.

Workup

  1. customThe solvent was removed in vacuo
  2. customleaving a colorless, viscous oil
  3. customThe oil was then purified by an ion exchange chromatography (Dowex-1×8)
  4. customFractions (visualized with iodine or ninhydrin) were collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82be5a75802f45d7bc7b9ffc7d168e97
Source dataset
uspto-grants-1993_02
Patent number
US05187279

Reaction notes

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