Potassium tert-butoxide → t-Butyl methyl-(4-cyanocyclohexyl)carbamate

HRID 906670노트

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HRID 906670 반응식
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].C1(C)C(S([CH2:26][N+:27]#[C-])(=O)=O)=CC=CC=1.CC(C)([O-])C.[K+]>O1CCCC1>[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH:13]([C:26]#[N:27])[CH2:12][CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]

참가 물질

5

반응물 3

HCID 23665647Potassium tert-butoxideHCID 24820328tert-butyl N-methyl-N-(4-oxocyclohexyl)carbamateHCID 53627694Toluenesulfonylmethyl isocyanide

생성물 1

HCID 66725780t-Butyl methyl-(4-cyanocyclohexyl)carbamate수율 30%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

t-Butyl methyl-(4-oxocyclohexyl)carbamate (4.54 g, 20 mmol) and toluenesulphonylmethyl isocyanide (5.07 g, 26 mmol) were dissolved in dry tetrahydrofuran (100 ml) and cooled to 0° C. Potassium tert-butoxide (5.16 g, 46 mmol) was added slowly and the mixture was allowed to warm to 20° C. and stir for 3 hours. The reaction mixture was evaporated to dryness and partitioned between ethyl acetate (150 ml) and water (50 ml). The organic layer was separated, dried over magnesium sulfate and evaporated. The crude product was chromatographed on a silica gel eluting with ethyl acetate/hexane (66:34) to give 1.43 g of tert-butyl methyl-(4-cyanocyclohexyl)carbamate.

후처리

  1. temperatureto warm to 20° C.
  2. customThe reaction mixture was evaporated to dryness
  3. custompartitioned between ethyl acetate (150 ml) and water (50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe crude product was chromatographed on a silica gel eluting with ethyl acetate/hexane (66:34)

출처 및 근거

ORD 기록
ord-95c1d52933144b5ba2f9442ff7429629
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013003B2

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