Sodium hydride → HCID 67999277, compound

HRID 932193Notes

Reaction equation

HRID 932193 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].[Si:14]([O:31][CH2:32][C@@H:33]([N:36]1[C@H:41]([C:42]2[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=2)[C@@H:40]([C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([Cl:55])[CH:50]=2)[CH2:39][C@:38]([CH3:58])([CH:56]=O)[C:37]1=[O:59])[CH2:34][CH3:35])([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[Si:14]([O:31][CH2:32][C@@H:33]([N:36]1[C@H:41]([C:42]2[CH:43]=[CH:44][C:45]([Cl:48])=[CH:46][CH:47]=2)[C@@H:40]([C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([Cl:55])[CH:50]=2)[CH2:39][C@@:38](/[CH:58]=[CH:7]/[C:5]([O:4][CH3:3])=[O:6])([CH3:56])[C:37]1=[O:59])[CH2:34][CH3:35])([C:27]([CH3:30])([CH3:29])[CH3:28])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 86660735HCID 86660735, compound

Product 1

HCID 67999277HCID 67999277, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of THF (4 mL) and sodium hydride (16 mg, 0.40 mmol, 60% dispersion in oil) under a nitrogen atmosphere at 0° C. was added trimethyl phosphonoacetate (61 μL, 0.43 mmol) dropwise over 30 seconds. The mixture was allowed to warm to rt for 30 minutes. A solution of (3R,5R,6S)-1-((S)-1-(tert-butyldiphenylsilyloxy)butan-2-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidine-3-carbaldehyde (205 mg, 0.305 mmol; Example 248, Step C) in THF (3 mL) was added. The resulting mixture was stirred at rt for 2 hours. The reaction was partitioned between EtOAc (80 mL) and water (40 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography (SiO2, hexanes:EtOAc, 1:0 to 8:2) gave the title compound. Mass Spectrum (ESI) m/z=728.2 (M+1).

Workup

  1. customThe reaction was partitioned between EtOAc (80 mL) and water (40 mL)
  2. dry with materialThe separated organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5301e22cdf1d421f80c9e8c19def5f62
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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