Sodium hydride → HCID 57925982, compound

HRID 1013503Notes

Reaction equation

HRID 1013503 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:19]=[CH:18][C:8]([CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][CH:6]=1.[CH:20]([P:23](=[O:29])([CH:26]([CH3:28])[CH3:27])[CH:24]=[CH2:25])([CH3:22])[CH3:21]>C1COCC1>[CH:20]([P:23]([CH2:24][CH2:25][N:10]([CH2:9][C:8]1[CH:18]=[CH:19][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:14])[CH3:15])([CH:26]([CH3:28])[CH3:27])=[O:29])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 141041591,1-Dimethylethyl N-[(4-methoxyphenyl)methyl]carbamateHCID 57925973HCID 57925973, compound

Product 1

HCID 57925982HCID 57925982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60%, 157 mg, 3.93 mmol) in THF (5 mL) at 0° C. was added tert-butyl (4-methoxybenzyl)carbamate (889 mg, 3.75 mmol) in THF (5 mL). After stirring for 30 minutes at 0° C., diisopropyl(vinyl)phosphine oxide (300 mg, 1.873 mmol) in THF (3 mL) was added. The reaction was allowed to slowly warn to room temperature and subsequently heated to 60° C. for 3 h. The mixture was quenched with saturated NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/EtOAc) afforded the title compound as a pale yellow oil. MS: cal'd 398 (MH+), exp 398 (MH+).

Workup

  1. customto slowly warn to room temperature
  2. temperaturesubsequently heated to 60° C. for 3 h
  3. customThe mixture was quenched with saturated NH4Cl
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-12648c6b36244fa1980d7e507476486e
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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