Diisopropylethylamine → HCID 178428944, compound

HRID 1013810Notes

Reaction equation

HRID 1013810 reaction equation
[CH2:1]([C@@H:8]1[CH2:12]O[C:10](=O)[N:9]1[C:14](=[O:36])[C@H:15]([CH2:19][C:20]1[C:25]([CH3:26])=[CH:24][C:23]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:22][C:21]=1[CH3:35])[CH2:16]C=O)[C:2]1[CH:7]=[CH:6]C=C[CH:3]=1.[N:37]1[NH:38]C=C2C=1CCC(N)C2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)C(C)C)(C)C>ClC(Cl)C.C(#N)C>[CH2:28]([O:27][C:23]1[CH:22]=[C:21]([CH3:35])[C:20]([CH2:19][C@@H:15]2[CH2:16][CH2:10][N:9]([CH:8]3[CH2:12][CH2:6][C:7]4[C:2](=[CH:3][NH:37][N:38]=4)[CH2:1]3)[C:14]2=[O:36])=[C:25]([CH3:26])[CH:24]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86629987HCID 86629987, compoundHCID 178507369HCID 178507369, compound

Product 1

HCID 178428944HCID 178428944, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Combine a solution of (R)-4-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-3-(4-benzyloxy-2,6-dimethyl-benzyl)-4-oxo-butyraldehyde (3.0 g, 6.2 mmol) and racemic 4,5,6,7-Tetrahydro-2H-indazol-5-ylamine (0.85 g, 6.2 mmol) in Dichloroethane (50 mL) and Acetonitrile (50 mL). Treat the solution with sodium triacetoxyborohydride (6.6 g, 31 mmol) and stir 1 hr at room temperature. Treat the reaction with N,N-Diisopropylethylamine (5.6 mL, 31 mmol) and stir overnight at room temperature. Concentrate the reaction to a residue. Quench the residue with saturated sodium carbonate and extract with EtOAc. Wash the organic with brine, dry over MgSO4, filter, and remove the solvent. Purify the crude by silica gel column chromatography using CH2Cl2 and 2M Ammonia in MeOH to elute the pure product. Remove the solvent to afford 1.66 g (62%) of desired product. MS (m/e): 430 (M+1).

Workup

  1. additionTreat
  2. stirringstir overnight at room temperature
  3. concentrationConcentrate
  4. customthe reaction to a residue
  5. customQuench the residue with saturated sodium carbonate
  6. extractionextract with EtOAc
  7. washWash the organic with brine
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. customremove the solvent
  11. customPurify the crude by silica gel column chromatography
  12. washto elute the pure product
  13. customRemove the solvent

Sources & evidence

ORD record
ord-c1e0056412ce4f99b8333e13f2076abe
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

Loading…