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

HRID 1501814노트

반응식

HRID 1501814 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fbaee89815b44834ba7bff66499e9fa0
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206198B2

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