Hydrochloric Acid → HCID 13110167, compound

HRID 1045655Notes

Reaction equation

HRID 1045655 reaction equation
[BH4-].[Na+].[Cl:3][CH2:4][C:5]([NH:7][CH:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])=[O:6].O.Cl>CO>[Cl:3][CH2:4][C:5]([NH:7][C@@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@H:9]1[OH:18])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 132930622-Chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

Product 1

HCID 13110167HCID 13110167, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.93 g, 24.6 mmol) was added to a solution of 2-chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (2.9 μg, 12.2 mmol) in methanol (30 ml). When the reaction was complete (checked by thin layer chromatography), excess reagent was decomposed by the addition of water and pH was adjusted to 5-6 with 3N aqueous hydrochloric acid. The solution was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford 2-chloro-N-((1RS,2RS)-trans-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-acetamide (2.92 g, 12.2 mmol, 100%) as white crystals.

Workup

  1. customThe solution was partitioned between water and chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

Sources & evidence

ORD record
ord-eb6b6baae0fa490ba7699433f4a7af9f
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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