Imidazole → HCID 178477596, compound

HRID 1044386Notes

Reaction equation

HRID 1044386 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:12][CH2:11][C@:10]3([CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:19])[CH2:13]3)[C:9]2=[O:28])[CH2:4][CH2:3]1.CN(C)C=O.N1C=CN=C1.Cl[Si:40]([CH2:45][CH3:46])([CH2:43][CH3:44])[CH2:41][CH3:42]>>[O:28]=[C:9]1[C@@:10]2([CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[O:19])[CH2:13]2)[CH2:11][CH2:12][N:8]1[C@H:5]1[CH2:4][CH2:3][C@H:2]([O:1][Si:40]([CH2:45][CH3:46])([CH2:43][CH3:44])[CH2:41][CH3:42])[CH2:7][CH2:6]1

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 13819ChlorotriethylsilaneHCID 178525119HCID 178525119, compound

Product 1

HCID 178477596HCID 178477596, compound

Procedure

To a solution of benzyl (5S)-2-(trans-4-hydroxycyclohexyl)-1-oxo-2,7-diazaspiro[4.5]decane-7-carboxylate (2.0 g, 0.0052 mol) in N,N-dimethylformamide (5 mL, 0.06 mol) were added 1H-imidazole (0.986 g, 0.0145 mol) and chlorotriethylsilane (1.13 mL, 0.00673 mol) at rt. After stirring for 2 h ice-water was added and the resulting mixture was stirred at room temperature for 30 minutes and extracted three times with AcOEt. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated. The residual oil was purified by column chromatography using 30% by volume AcOEt in hexanes.

Workup

  1. additionwas added
  2. extractionextracted three times with AcOEt
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residual oil was purified by column chromatography

Sources & evidence

ORD record
ord-d579e43d120e4831af53f66a815b8d76
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

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