Methanol → HCID 67076690, compound

HRID 521531Notes

Reaction equation

HRID 521531 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([CH:24]=[O:25])[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[BH4-].[Na+].CO>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([CH2:24][OH:25])[CH:17]=2)[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)=[O:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86654801HCID 86654801, compound

Product 1

HCID 67076690HCID 67076690, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of step 1 (0.500 g, 1.42 mmol) was dissolved in THF (5 ml) and cooled in an ice bath. Sodium borohydride (0.164 g, 4.25 mmol) was added. Subsequently methanol (2 ml) was added dropwise. After 1 h, the volatiles were evaporated, the residue was partitioned between diethyl ether and a saturated sodium hydrogencarbonate solution, and the aqueous phase extracted with diethyl ether. The combined organic phases were dried over sodium sulfate and evaporated to dryness.

Workup

  1. temperaturecooled in an ice bath
  2. customthe volatiles were evaporated
  3. customthe residue was partitioned between diethyl ether
  4. extractiona saturated sodium hydrogencarbonate solution, and the aqueous phase extracted with diethyl ether
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f3658bbb1cb5434194eaa597baec6c90
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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