Methanol → Tert-butyl 2-(4-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1848501Notes

Reaction equation

HRID 1848501 reaction equation
[CH:1]([C:3]1[C:7](=[O:8])[O:6][CH2:5][C:4]=1[N:9]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[C:10]1=[O:26])=[O:2].CO.[BH4-].[Na+]>C1COCC1>[OH:2][CH2:1][C:3]1[C:7](=[O:8])[O:6][CH2:5][C:4]=1[N:9]1[CH2:13][CH2:12][C:11]2([CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:17][CH2:18]2)[C:10]1=[O:26]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86709510Tert-butyl 2-(4-formyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 86709511Tert-butyl 2-(4-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-butyl 2-(4-formyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (1.18 g, 3.24 mmol) was dissolved in THF (13 mL) and MeOH (13 mL) and the mixture was cooled to −78° C. and stirred for 15 min. Sodium borohydride (0.147 g, 3.89 mmol) was added in two equal portions and the resulting mixture was stirred for ˜15 min. at −78° C. LC-MS after 15 minutes stirring at −78° C. showed complete consumption of starting material. The reaction mixture was diluted with ethyl acetate and quenched with aqueous ammonium chloride solution at −78° C. The aqueous layer was extracted with EtOAc (2×), combined organic layers were washed with water, brine, then dried (MgSO4) and filtered, and the solvent was evaporated under reduced pressure to obtain the product, which was taken to the next step without purification.

Workup

  1. stirringthe resulting mixture was stirred for ˜15 min. at −78° C
  2. stirringLC-MS after 15 minutes stirring at −78° C.
  3. customconsumption of starting material
  4. additionThe reaction mixture was diluted with ethyl acetate
  5. customquenched with aqueous ammonium chloride solution at −78° C
  6. extractionThe aqueous layer was extracted with EtOAc (2×)
  7. washwere washed with water, brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated under reduced pressure
  11. customto obtain the product, which
  12. customwas taken to the next step without purification

Sources & evidence

ORD record
ord-0211c732b9b64687a2d86a69dbca4575
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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