Sodium borohydride → HCID 24984412, compound

HRID 1724072Notes

Reaction equation

HRID 1724072 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]3[CH2:23][C:22]4([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[O:21][C:20]3=[O:29])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)[CH:2]=C.[BH4-].[Na+].C(Cl)Cl.C[OH:36]>C(=O)=O.CC(C)=O>[OH:36][CH2:2][CH2:1][O:4][CH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][N:19]3[CH2:23][C:22]4([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)[O:21][C:20]3=[O:29])=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226129Dichloromethane methanolHCID 24983950HCID 24983950, compound

Product 1

HCID 24984412HCID 24984412, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 18522661Acetone cardiceSolvent

Conditions

Temperature
0 °C

Procedure

3-(3′-Allyloxymethyl-biphenyl-4-ylmethyl)-1-oxa-3-aza-spiro[4.5]decan-2-one (260 mg, 0.664 mmol) was dissolved in DCM/methanol (4:1, 7.5 mL) and was cooled to −78° C. in dry ice-acetone bath. O3 was bubbled through the solution for 15 min. Thin layer chromatography (TLC) confirmed the completion of the reaction at this stage. The DCM was evaporated in vacuo; ethanol (5 mL) was added and the solution was cooled in ice-water bath to 0° C. NaBH4 (175 mg, 7 eq.) was added and the reaction was stirred at the temperature of 0˜5° C. for one hour then at room temperature for 1.5 hour. The reaction mixture was quenched with saturated NaHCO3 aqueous solution. The aqueous phase was extracted with DCM (3×8 mL), the combined organic phases were washed with brine (5 mL), dried over sodium sulfate and concentrated. The crude residue was purified on silica gel eluting with 20˜50% ethyl acetate in hexane to give the product (134 mg, 51%). 1H NMR (300 MHz, CDCl3): δ (ppm) 7.59 (d, 3H), 7.52 (d, 1H), 7.41 (t, 1H), 7.32 (d, 3H), 4.85 (s, 2H), 4.45 (s, 2H), 3.77 (br, 2H), 3.62 (t, 2H), 3.12 (s, 2H), 2.48 (br, 1H), 1.72 (m, 4H), 1.5 (m, 6H).

Workup

  1. customO3 was bubbled through the solution for 15 min
  2. customthe completion of the reaction at this stage
  3. customThe DCM was evaporated in vacuo
  4. additionethanol (5 mL) was added
  5. waitat room temperature for 1.5 hour
  6. customThe reaction mixture was quenched with saturated NaHCO3 aqueous solution
  7. extractionThe aqueous phase was extracted with DCM (3×8 mL)
  8. washthe combined organic phases were washed with brine (5 mL)
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe crude residue was purified on silica gel eluting with 20˜50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d506ba2015944d4c93a398d6a4643d24
Source dataset
uspto-grants-2009_02
Patent number
US07485722B2

Reaction notes

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