Dicyclohexylcarbodiimide → HCID 178442538, 화합물

HRID 704286노트

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HRID 704286 반응식
[C:1]([C:3]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)#[N:2].O1C2(CCC(C3CCC(=O)CC3)CC2)OCC1.S(C[N+]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[Li+].CC([N-]C(C)C)C.C(Br)CCCCCC.[BH4-].[Na+].[CH2:71]([C@H:76]1[CH2:81][CH2:80][C@H:79]([C:82](O)=[O:83])[CH2:78][CH2:77]1)[CH2:72][CH2:73][CH2:74][CH3:75].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([C:3]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([O:15][C:82]([C@H:79]3[CH2:80][CH2:81][C@H:76]([CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[CH2:77][CH2:78]3)=[O:83])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)#[N:2]

참가 물질

11

반응물 8

HCID 10868DicyclohexylcarbodiimideHCID 123691-BromoheptaneHCID 161915Tosylmethyl isocyanideHCID 8109134-(1,4-Dioxa-spiro(4.5)dec-8-yl)-cyclohexanoneHCID 2724682Lithium diisopropylamideHCID 4311764Sodium borohydrideHCID 200761544-Cyano-4-heptyl-4'-hydroxybicyclohexaneHCID 178444557HCID 178444557, 화합물

생성물 1

HCID 178442538HCID 178442538, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

1 g of 4-dimethylaminopyridine and 30.3 g (0.1 mole) of 4-cyano-4-heptyl-4'-hydroxybicyclohexane (obtainable from 4-(1,4-dioxaspiro[4,5]dec-8-yl)-cyclohexanone by introduction of the nitrile group with tosylmethyl isocyanide (TOSMIC), alkylation with LDA (diisopropylamine/butyl-lithium) and heptyl bromide, detachment of the keto-protective group, reduction of the ketone with NaBH4 to the alcohol and separation of the isomers) are added to 19.8 g (0.1 mole) of trans-4-pentylcyclohexanecarboxylic acid in 75 ml of CH2Cl2, with stirring. A solution of 27.7 g (0.105 mole) of dicyclo-hexylcarbodiimide in 50 ml of methylene chloride is added dropwise at 0°, while controlling the temperature, and the mixture is then stirred at room temperature for a further hour. The urea precipitated is separated off and the methylene chloride phase is washed with dilute HCl and saturated NaHCO3 solution and dried. The product is then purified by filtration over a short silica gel column and by crystallisation. 4-Cyano-4-heptyl-4'-(trans-4-pentylcyclohexylcarbonyloxy)-bicyclohexane is obtained.

후처리

  1. stirringthe mixture is then stirred at room temperature for a further hour
  2. customThe urea precipitated
  3. customis separated off
  4. washthe methylene chloride phase is washed with dilute HCl and saturated NaHCO3 solution
  5. customdried
  6. filtrationThe product is then purified by filtration over a short silica gel column and by crystallisation

출처 및 근거

ORD 기록
ord-13dc750527bf44dbada3076a853a38b0
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04985583

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