Triacetoxyperiodinane → tert-Butyl N-(3-formylcyclohexyl)carbamate

HRID 712036노트

반응식

HRID 712036 반응식
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:4]1)=[O:1]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 22106830tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate

생성물 1

HCID 86717490tert-Butyl N-(3-formylcyclohexyl)carbamate수율 60%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl [3-(hydroxymethyl)cyclohexyl]carbamate (0.51 g, 2.2 mmol) in methylene chloride (10 mL) at 0° C. was added Dess-Martin periodinane (1.1 g, 2.7 mmol). The mixture was stirred at room temperature for 2 h. The reaction was quenched with aq. 1N NaOH solution and extracted with methylene chloride. The combined organic layers were washed with water and then brine, dried over MgSO4, concentrated, and then purified on silica gel column (eluting with 20-50% EtOAc in hexanes) to give the desired product (0.3 g, 59%). LCMS calculated for C12H21NO3Na (M+Na)+: m/z=250.2. Found: 250.1.

후처리

  1. customThe reaction was quenched with aq. 1N NaOH solution
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers were washed with water
  4. dry with materialbrine, dried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica gel column (eluting with 20-50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-c041ab20dc7d4b129b23dfde65ddf302
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181271B2

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