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

HRID 712036ノート

反応式

HRID 712036 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c041ab20dc7d4b129b23dfde65ddf302
出典データセット
uspto-grants-2015_11
特許番号
US09181271B2

反応ノート

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