Sodium hydride → HCID 69001680, compound

HRID 1909737Notes

Reaction equation

HRID 1909737 reaction equation
[H-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.[C:20]([O:24][C:25]([N:27]1[CH2:31][CH2:30][CH2:29][C@@H:28]1[CH2:32]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:26])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[C:20]([O:24][C:25]([N:27]1[CH2:31][CH2:30][CH2:29][C@@H:28]1[CH2:32][O:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][C:4]2[S:3][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=2)=[CH:18][CH:17]=1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11760051(R)-tert-Butyl 2-((tosyloxy)methyl)pyrrolidine-1-carboxylateHCID 431414064-(2-Benzothiazolylmethyl)phenol

Product 1

HCID 69001680HCID 69001680, compoundYield 75.4%

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 added the product from step 1 (241 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 95° C. and stirred at 95° 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 (320 mg, 70%); 1H NMR (400 MHz, CDCl3); δ 1.47 (s, 9H), 1.81-2.11 (m, 4H), 3.32-3.47 (m, 2H), 3.70-4.20 (m, 3H), 4.37 (s, 2H), 6.84-6.97 (m, 4H), 7.33 (t, J=7.6, 1H), 7.45 (t, J=7.6, 1H), 7.78 (d, J=8.0, 1H), 7.98 (d, J=8.4, 1H).

Workup

  1. temperaturethen cooled to 0° C
  2. temperatureThe resulting mixture was allowed warm to rt
  3. stirringstir at rt for 30 min
  4. temperaturewas heated to 95° C.
  5. stirringstirred at 95° C. for 16 h
  6. temperatureAfter cooling to rt
  7. stirringto stir at 0° C. for 30 min
  8. customThe solid which formed
  9. filtrationwas filtered out
  10. customdried through air

Sources & evidence

ORD record
ord-8569c30ff0a2421bb17782a5521fc33c
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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