Imidazole → HCID 69035707, compound

HRID 1270415Notes

Reaction equation

HRID 1270415 reaction equation
[OH:1][C@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[C@@H:7]([CH2:11][C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][CH:13]=3)[NH:8][C:9](=[O:10])[C@@H:4]2[CH2:3]1.N1C=CN=C1.[C:28]([Si:32](Cl)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:31])([CH3:30])[CH3:29]>CN(C)C=O>[Si:32]([O:1][C@H:2]1[CH2:22][N:5]2[C:6](=[O:21])[C@@H:7]([CH2:11][C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[NH:14][CH:13]=3)[NH:8][C:9](=[O:10])[C@@H:4]2[CH2:3]1)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 69035438HCID 69035438, compound

Product 1

HCID 69035707HCID 69035707, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3R,7R,8aS)-7-hydroxy-3-(1H-indol-3-ylmethyl)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione (2.5 g) in dimethylformamide (30 mL) was added imidazole (1.7 g) and tert-butyl-chloro-diphenylsilane (4.35 mL). The resulting mixture was stirred overnight at room temperature and then partitioned between water and ethyl acetate. The organic layer was dried, filtered and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, EtOAc) to afford (3R,7R,8aS)-7-(tert-butyl-diphenylsilanyloxy)-3-(1H-indol-3-ylmethyl)-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione (4.6 g, 99%) (intermediate 7).

Workup

  1. custompartitioned between water and ethyl acetate
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-916de31c503644c7a70750732e76fd5d
Source dataset
uspto-grants-2007_04
Patent number
US07202238B2

Reaction notes

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