Ammonia → HCID 69415666, compound

HRID 2184379Notes

Reaction equation

HRID 2184379 reaction equation
[C:1]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[CH2:14]O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(C1NC=[CH:26][N:27]=1)(C1NC=CN=1)=O.N.C1C[O:32]CC1>>[C:1]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[CH2:14][C:26](=[O:32])[NH2:27])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 11275979N-Boc-trans-4-hydroxy-L-prolinol

Product 1

HCID 69415666HCID 69415666, compoundYield 31%

Procedure

To N-Boc-(2S,4R)-4-hydroxy-2-hydroxymethylpyrrolidine (0.105 g in THF (5 ml) cooled to 0° C. under argon was added carbonyl diimidazole (121 mg). After 3 h aqueous ammonia (20 M, 0.25 ml) was added and the reaction stirred for 17 h. The reaction mixture was evaporated to dryness under reduced pressure and the residue purified by chromatography on silica eluting with 80-100% ethyl acetate in hexane to give the title product as a colourless gum (45 mg, 31%); NMR (CDCl3) 1.47 (s, 9H), 2.05 (m, 3H), 3.4-3.6 (m, 2H), 4.154.3 (m, 3H), 4.45 (m, 1H), 4.75 (bs, 2H).

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. customthe residue purified by chromatography on silica eluting with 80-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-168c036586ca4f09ac3bd7160382cf0a
Source dataset
uspto-grants-2005_05
Patent number
US06900345B2

Reaction notes

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