Hydrochloric Acid → HCID 13110165, compound

HRID 1045657Notes

Reaction equation

HRID 1045657 reaction equation
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[Cl:15][CH2:16][C:17]([NH:19][CH:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30])=[O:18].O.Cl>O1CCCC1>[Cl:15][CH2:16][C:17]([NH:19][C@H:20]1[CH2:29][CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@H:21]1[OH:30])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3611392Lithium tri-s-butylborohydrideHCID 132930622-Chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

Product 1

HCID 13110165HCID 13110165, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium tri-sec-butylborohydride (1.0 M solution in tetrahydrofuran, 70 ml, 70 mmol) was added to a solution of 2-chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (7.58 g, 31.9 mmol) in tetrahydrofuran (500 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 residue 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,2SR)-cis-1-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-acetamide (5.4 g, 22.6 mmol, 71%) as white crystals.

Workup

  1. customThe residue 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-81e8e9b2d3a64288a9308c00e41c1d82
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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