Hydrochloric Acid → HCID 57869862, compound

HRID 1045663Notes

Reaction equation

HRID 1045663 reaction equation
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[Cl:15][CH2:16][C:17]([NH:19][CH:20]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:22][CH2:21]1)=[O:18].O.Cl>O1CCCC1>[Cl:15][CH2:16][C:17]([NH:19][C@H:20]1[C@@H:29]([OH:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:22][CH2:21]1)=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3611392Lithium tri-s-butylborohydrideHCID 57869938HCID 57869938, compound

Product 1

HCID 57869862HCID 57869862, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium tri-sec-butylborohydride (1.0 M solution in tetrahydrofuran, 190 ml, 190 mmol) was added to a solution of 2-chloro-N-(4-oxo-chroman-3-yl)-acetamide (22.6 g, 94.3 mol) in tetrahydrofuran (1000 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-((3RS,4SR)-cis-4-hydroxychroman-3-yl)-acetamide (19 g, 78.6 mmol, 83%) 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-f857c56d53c24578a96b5bf63026b304
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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