Lithium borohydride → HCID 66608257, compound

HRID 1529550Notes

Reaction equation

HRID 1529550 reaction equation
[BH4-].[Li+].C[O:4][C:5]([C:7]1[O:8][C:9]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][C:10]=2[N:11]=1)=O>CO.C1COCC1.[NH4+].[Cl-]>[CH3:21][C:18]([O:17][C:15]([N:13]1[CH2:14][C:9]2[O:8][C:7]([CH2:5][OH:4])=[N:11][C:10]=2[CH2:12]1)=[O:16])([CH3:19])[CH3:20]

Participants

6

Reactant 2

HCID 4148881Lithium borohydrideHCID 66608460HCID 66608460, compound

Product 1

HCID 66608257HCID 66608257, compoundYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Lithium borohydride (0.015 g, 0.72 mmol) was added to a stirred solution of 4,6-dihydro-5H-pyrrolo[3,4-d]oxazole-2,5-dicarboxylic acid 5-(1,1-dimethylethyl) 2-methyl ester (0.064 g, 0.24 mmol) in a mixture of MeOH (0.6 mL) and THF (1 mL) at 0° C. The mixture was stirred at room temperature for 30 minutes, diluted with a saturated solution of NH4Cl and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 4,6-dihydro-2-(hydroxymethyl)-5H-pyrrolo[3,4-d]oxazole-5-carboxylic acid 1,1-dimethylethyl ester (0.055 g, 96% yield) as a clear oil that was used in the next step without further purification. C11H16N2O4 LCMS: Rt 1.29, m/z 241 [M+H]+ (using method, LC-MS Method 6).

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-926c02e198c740b08592c4def814e0d3
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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