Sodium borohydride → HCID 67515018, compound

HRID 1770762Notes

Reaction equation

HRID 1770762 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:23])([CH3:22])[CH2:13][C:14](=[O:21])[CH2:15][C:16](OCC)=[O:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[OH:21][CH:14]([CH2:15][CH2:16][OH:17])[CH2:13][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67508114HCID 67508114, compound

Product 1

HCID 67515018HCID 67515018, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-(benzyloxycarbonylamino)-5-methyl-3-oxohexanoate (3.49, 10.9 mmol) was dissolved in ethanol (100 ml). Sodium borohydride (1.64 g, 43.4 mmol) was added to the mixture, and the reaction mixture was stirred for 3 hours at room temperature. The reaction was quenched with 1 N HCl, and the mixture was stirred for 1 hour. The mixture was extracted with ethylacetate, and the combined organic layers were dried over sodium sulfate, filtered, and purified by column chromatography (0 to 4% methanol on dichloromethane) to give 2.14 g (70%) of the title compound.

Workup

  1. customThe reaction was quenched with 1 N HCl
  2. stirringthe mixture was stirred for 1 hour
  3. extractionThe mixture was extracted with ethylacetate
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. custompurified by column chromatography (0 to 4% methanol on dichloromethane)

Sources & evidence

ORD record
ord-96d0914212db4294b2c2a4e23e4fd24a
Source dataset
uspto-grants-2016_02
Patent number
US09248117B2

Reaction notes

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