Ozone → N-(3-Hydroxy-1-phenylpropyl)-N-methylbenzenesulfonamide

HRID 860164

반응식

HRID 860164 반응식
[O:1]=[O+][O-].[CH3:4][N:5]([CH:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:16][CH:17]=C)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7].[BH4-].[Na+]>CO>[OH:1][CH2:17][CH2:16][CH:15]([N:5]([CH3:4])[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 69447982N-Methyl-N-(1-phenylbut-3-enyl)benzenesulfonamide

생성물 1

HCID 69444505N-(3-Hydroxy-1-phenylpropyl)-N-methylbenzenesulfonamide수율 93%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Ozone was bubbled through a solution of the product of Step 1 (1.0 g, 3.3 mmol) in MeOH (50 mL) at −78° C. for 30 min, then after appearance of a pale blue colour, the reaction was purged with N2 for several minutes and NaBH4 (245 mg, 6.6 mmol) was added. The resulting solution was allowed to warm to RT and stirred for a further 15 min at RT. The reaction was quenched by the addition of NH4Cl solution (10 mL) and then concentrated under reduced pressure. H2O (50 mL) was added and then extracted with EtOAc (100 ml and 50 mL). The combined organic extracts were dried (MgSO4) and then concentrated under reduced pressure to yield the alcohol (0.94 g, 93%). 1H NMR (CDCl3, 400 MHz) δ 7.81 (2H, d, J=7.2 Hz), 7.65–7.45 (3H, m), 7.20–7.13 (3H, m), 6.93 (2H, d, J=7.5 Hz), 5.25 (1H, dd, J=9.1, 6.3 Hz), 3.90–3.80 (1H, m), 3.74–3.59 (1H, m), 2.63 (3H, s), 2.13–1.98 (2H, m).

후처리

  1. customafter appearance of a pale blue colour, the reaction was purged with N2 for several minutes
  2. customThe reaction was quenched by the addition of NH4Cl solution (10 mL)
  3. concentrationconcentrated under reduced pressure
  4. additionH2O (50 mL) was added
  5. extractionextracted with EtOAc (100 ml and 50 mL)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5199f67ea3c74e9b95806897c31fed38
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153868B2

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