Sodium Hydroxide → N-{[(1S,2R)-2-formyl-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide

HRID 2099274노트

반응식

HRID 2099274 반응식
[OH:1][CH2:2][C@@H:3]1[CH2:5][C@@:4]1([CH2:12][N:13]([CH3:23])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.CC(O)(C)C.C(OCC)C>[CH:2]([C@@H:3]1[CH2:5][C@@:4]1([CH2:12][N:13]([CH3:23])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:1]

참가 물질

7

반응물 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 57794737N-{[(1S,2R)-2-(hydroxymethyl)-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide

생성물 1

HCID 57794728N-{[(1S,2R)-2-formyl-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide수율 45.1%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회HCID 6386tert-Butanol용매

실험 절차

N-{[(1S,2R)-2-(hydroxymethyl)-1-phenylcyclopropyl]methyl}-N-methylbenzenesulfonamide (600 mg, 1.82 mmol), accessed via the method of preparation 7A, was dissolved in 18 mL DCM with 270 uL 2-methylpropan-2-ol and treated with Dess-Martin Periodinane (1.23 g, 2.90 mmol, 1.6 eq) at ambient temperature for 16 h. The reaction mixture was diluted with 42 mL diethyl ether and treated with 22 mL 1N NaOH at ambient temperature for 15 min. The organic phase was separated, the aqueous phase extracted twice with diethyl ether, the organic phases combined, washed with brine, dried over MgSO4, filtered and concentrated to a colorless oil. The crude material was purified by flash chromatography (SiO2, eluted successively with DCM, EtOAc/hexanes (1:4)) to the title product (270 mg, 0.82 mmol, 45%) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 9.82 (d, J=3.8 Hz, 1H), 7.65-7.28 (m, 10H), 3.53-3.43 (m, 2H), 2.42 (s, 3H), 2.34-2.32 (m, 1H), 1.90-1.87 (m, 1H), 1.70-1.66 (m, 1H).

후처리

  1. customThe organic phase was separated
  2. extractionthe aqueous phase extracted twice with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to a colorless oil
  7. customThe crude material was purified by flash chromatography (SiO2

출처 및 근거

ORD 기록
ord-155b4b773e734d2991b11fd14a471c53
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569579B2

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