Sodium Bicarbonate → HCID 58782546, compound

HRID 1374476Notes

Reaction equation

HRID 1374476 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]([N:11]1[CH2:18][CH:17]2[CH:13]([CH2:14][NH:15][CH2:16]2)[CH2:12]1)=[O:10].O=[C:20]([CH3:37])[CH2:21][CH:22]([NH:29][C:30]([CH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.C1COCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].O>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[C:9]([N:11]1[CH2:18][CH:17]2[CH2:16][N:15]([CH:20]([CH3:37])[CH2:21][C@H:22]([NH:29][C:30]([CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:31])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:14][CH:13]2[CH2:12]1)=[O:10]

Participants

9

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21076152HCID 21076152, compoundHCID 69436264HCID 69436264, compound

Product 1

HCID 58782546HCID 58782546, compound

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

step 5—To a solution of (2,6-dimethyl-phenyl)-(hexahydro-pyrrolo[3,4-c]pyrrol-2-yl)-methanone (66, 0.12 g, 0.52 mmol) in DCM (7 mL) and THF (7 mL) was added cyclopentanecarboxylic acid (3-oxo-1-phenyl-butyl)-amide (85d, 0.15 g, 0.57 mmol). Titanium tetraisopropoxide (0.34 mL, 1.15 mmol) was added to the mixture. After 30 min NaBH(OAc)3 (0.16 g, 0.78 mmol) was added and the mixture stirred at RT for 4 h. Saturated NaHCO3 was added to the mixture and it was stirred for 10 min. The mixture was extracted with DCM and the organic layer was dried (MgSO4), filtered and evaporated. The crude product was purified by SiO2 chromatography on silica gel eluting with DCM:MeOH:NH4OH (150:10:1) to afford I-75: ms (ES+) m/z 488 (M+H); Anal. (C31H41N3O2.0.3M H2O)C; calcd, 75.51; found 75.53; H; calcd, 8.50; found, 8.29; N; calcd, 8.52; found, 8.53.

Workup

  1. stirringwas stirred for 10 min
  2. extractionThe mixture was extracted with DCM
  3. dry with materialthe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by SiO2 chromatography on silica gel eluting with DCM:MeOH:NH4OH (150:10:1)
  7. customto afford I-75: ms (ES+) m/z 488 (M+H)

Sources & evidence

ORD record
ord-ce411700ffc64cb285357274e664be28
Source dataset
uspto-grants-2007_01
Patent number
US07164019B2

Reaction notes

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