Methanol → HCID 67606706, compound

HRID 1965206Notes

Reaction equation

HRID 1965206 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:7]2[CH2:20][CH2:21][N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:6]12)=O.[Li+].[BH4-].CO.O>C1COCC1>[C:26]([O:25][C:23]([N:22]1[CH:6]2[CH:7]([N:8]([C:10]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH2:9][CH:5]2[CH2:3][OH:2])[CH2:20][CH2:21]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 67280928Hexahydro-pyrrolo[3,2-b]pyrrole-1,3,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester 3-methyl ester

Product 1

HCID 67606706HCID 67606706, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ester 76 (2.7 g, 6.7 mmol) in THF (15 mL) was cooled to 0° C. and treated with LiBH4 (10 mL, 2M in THF). After 3 h, the solution was slowly treated with MeOH followed by H2O. The solution was then concentrated and diluted with EtOAc. The solution was slowly treated with 1M HCl until gas generation ceased. The solution was extracted with EtOAc, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was absorbed onto SiO2 and purified by flash chromatography (1:1 hexane/EtOAc to 1:2 hexane/EtOAc) to afford alcohol 77 (1.9 g, 75%) as a light yellow-colored oil. 1H NMR (CDCl3, 300 MHz): δ7.39-7.27 (m, 5H), 5.13-5.09 (m, 2H), 4.43-4.41 (m, 1H), 4.13-4.08 (m, 2H), 3.70-3.29 (m, 6H), 2.48-2.46 (m, 1H), 2.53-2.05 (m, 1H), 2.03-1.99 (m, 1H), 1.48 (s, 9H) ppm. Mass spectrum, m/z [377.5] (M+H)+.

Workup

  1. concentrationThe solution was then concentrated
  2. additiondiluted with EtOAc
  3. additionThe solution was slowly treated with 1M HCl until gas generation
  4. extractionThe solution was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was absorbed onto SiO2
  10. custompurified by flash chromatography (1:1 hexane/EtOAc to 1:2 hexane/EtOAc)

Sources & evidence

ORD record
ord-a82ff04ca5ee4b59a50172e9a1e8ac1a
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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