Ammonia → HCID 69415666, compound

HRID 1373154Notes

Reaction equation

HRID 1373154 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), 4.15–4.3 (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-69696dda312144cfb95214cbc87c0139
Source dataset
uspto-grants-2007_01
Patent number
US07160907B2

Reaction notes

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