Acetic Acid → (2S,3R,4R)-3,4-dihydroxypyrrolidine-2-carboxylic acid

HRID 2050667Notes

Reaction equation

HRID 2050667 reaction equation
C([C@H:8]1[C@@H:12]([OH:13])[CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[C@@H:9]1[C:24]([OH:26])=[O:25])C1C=CC=CC=1.C(O)(=[O:29])C>[Pd]>[OH:29][C@H:8]1[C@H:12]([OH:13])[CH2:11][NH:10][C@@H:9]1[C:24]([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 57152591HCID 57152591, compound

Product 1

HCID 452017(2S,3R,4R)-3,4-dihydroxypyrrolidine-2-carboxylic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(2S, 3R, 4R)-3-benzyl-N-benzyloxycarbonyl-4-hydroxyproline (17) (523 mg, 1.95 mmol) was dissolved in glacial acetic acid (12 ml) containing palladium black (100 mg) and stirred under hydrogen at atmospheric pressure for 48 hours. The solution was filtered and the solvent removed. Purification by flash chromatography (CMAW) and ion exchange resin gave (2S, 3R, 4R)-3,4-dihydroxyproline (220 mg, 93.5%) as a white crystalline solid, m.p. 220°-245° C. decomposed without melting (lit.37 250° dec.), [α]20D -12.2° (c, 0.83 in water) [lit.37 [α]D25 -19° (c, 0.4 in water)]; νmax (KBr disc) 3260, 1615 (CO), 1370, 1270, 1075, 1050 and 760 cm-1 ; 1H NMR δ (D2O) 3.35 (1H, d, H-5, J5,5' 12.5 Hz); 3.44 (1H, dd, H-5', J4,5' 3.7 Hz); 3.90 (1H, s, H-2); 4.14 (1H, dt, H-4, J3,4 1.2 Hz); 4.36 (1H, bs, H-3). 13C NMR (D2O) δ 51.71 (t, C-5); 66.33 (d, C-2); 74.75 (d, C-4); 79.14 (d, C-3); 171.86 (s, C-1). m/z: 124 (100%), 104 (77%), 148 (M+H+, 75%), 84 (67%).

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent removed
  3. customPurification by flash chromatography (CMAW) and ion exchange resin

Sources & evidence

ORD record
ord-af1cdc9cec004460ae7c2e21e95bf438
Source dataset
uspto-grants-1991_05
Patent number
US05013842

Reaction notes

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