Methanol → HCID 19605559, compound

HRID 1603436Notes

Reaction equation

HRID 1603436 reaction equation
[CH2:1]([N:8]1[CH2:14][CH:13]2[C:10]([C:15](OC(C3C=CC=CC=3)C3C=CC=CC=3)=[O:16])([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].[BH4-].[Na+].CO>O1CCCC1>[CH2:1]([N:8]1[CH2:14][CH:13]2[C:10]([CH2:15][OH:16])([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 19605564HCID 19605564, compound

Product 1

HCID 19605559HCID 19605559, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13 g of 3-benzyl-1-diphenylmethoxycarbonyl-3-azabicyclo[3.2.0]heptane was dissolved in 100 ml of tetrahydrofuran, and 2.8 g of lithium chloride was added thereto. After 2.5 g of sodium borohydride was added little by little, 30 ml of methanol was slowly added thereto and the resulting mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, mixed with ice water, and extracted with ethyl acetate. After the extract was mixed with 10% hydrochloric acid and stirred vigorously, the aqueous layer was separated. This aqueous layer was adjusted to pH 8 by the addition of a 10% aqueous solution of sodium hydroxide, and then extracted with ethyl acetate. After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (using a 4:1 mixture of n-hexane and acetone as the eluent) to obtain 5.4 g of 3-benzyl-1-hydroxymethyl-3-azabicyclo[3.2.0]heptane.

Workup

  1. additionwas slowly added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionmixed with ice water
  4. extractionextracted with ethyl acetate
  5. additionAfter the extract was mixed with 10% hydrochloric acid
  6. stirringstirred vigorously
  7. customthe aqueous layer was separated
  8. additionThis aqueous layer was adjusted to pH 8 by the addition of a 10% aqueous solution of sodium hydroxide
  9. extractionextracted with ethyl acetate
  10. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography (
  13. additiona 4:1 mixture of n-hexane and acetone as the eluent)

Sources & evidence

ORD record
ord-99a4f2dcf5f943cd971cf71122ee73c7
Source dataset
uspto-grants-1999_11
Patent number
US05990106

Reaction notes

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