Sodium hydride → HCID 68996388, compound

HRID 750056Notes

Reaction equation

HRID 750056 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@@H:26]1[CH2:30]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@@H:26]1[CH2:30][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([I:3])=[CH:17][CH:16]=2)=[CH:10][CH:11]=1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11760051(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylateHCID 19106773HCID 19106773, compound

Product 1

HCID 68996388HCID 68996388, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 25 mL vial which contained a suspension of NaH (60% in mineral oil, 60 mg, 1.5 mmol) in DMF (10 mL) was the product from step 3 (310 mg, 1 mmol) at 0° C. The mixture was allowed to warm to rt and stir at rt for 30 min then cooled to 0° C. To this reaction mixture was added (R)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (355 mg, 1 mmol) at 0° C. The resulting mixture was allowed warm to rt and stir at rt for 30 min and then was heated to 90° C. and stirred at 90° C. for 16 h. After cooling to rt, the mixture was poured onto 200 mL ice-water solution and this solution was allowed to stir at 0° C. for 30 min. The solid which formed was filtered out, dried through air to afford the title product (290 mg, 59%); 1H NMR (400 MHz, CDCl3); δ 1.47 (s, 9H), 1.79-2.08 (m, 4H), 3.26-3.46 (m, 2H), 3.70-3.93 (m, 1H), 3.85 (s, 2H), 4.02-4.19 (m, 2H), 6.82-6.88 (m, 2H), 6.91 (d, J=7.6 Hz, 2H), 7.04 (d, J=8.0 Hz, 2H), 7.58 (d, J=8.0 Hz, 2H):

Workup

  1. customat 0° C
  2. temperaturethen cooled to 0° C
  3. temperatureThe resulting mixture was allowed warm to rt
  4. stirringstir at rt for 30 min
  5. temperaturewas heated to 90° C.
  6. stirringstirred at 90° C. for 16 h
  7. temperatureAfter cooling to rt
  8. stirringto stir at 0° C. for 30 min
  9. customThe solid which formed
  10. filtrationwas filtered out
  11. customdried through air

Sources & evidence

ORD record
ord-18f26fc26ed94574b79fc3b1f809431b
Source dataset
uspto-grants-2008_07
Patent number
US07402684B2

Reaction notes

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