Ammonia → (R)-1-Cbz-2-(aminocarbonyl)piperidine

HRID 1155087

반응식

HRID 1155087 반응식
[N:1]1([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3](O)=[O:4].C([N:22](CC)CC)C.ClC(OCC(C)C)=O.N>C(OCC)(=O)C>[N:1]1([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([NH2:22])=[O:4]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 688346(2R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid

생성물 1

HCID 27281977(R)-1-Cbz-2-(aminocarbonyl)piperidine수율 88%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
-20 °C

실험 절차

13.15 g (50 mmoles) of Z-D-Pip-OH (L. Balaspiri et al.: Monatsh. Chem. 101, 177/1970/) are dissolved in 100 ml of ethyl acetate, 7.0 ml (50 mmoles) of triethylamine are added, and the solution is cooled to -20° C. 6.5 ml (50 mmoles) of isobutyl chloroformate are added dropwise to the stirred solution at the same temperature, thereafter the mixture is stirred for 15 minutes, and then gaseous ammonia is introduced into the mixture at -10° C. for 1.5 hours. The separated precipitate is filtered off, the filtrate is washed with n hydrochloric acid, n sodium hydrocarbonate solution and water, dried over anhydrous sodium sulfate and evaporated. The residue is crystallized from a mixture of ethyl acetate and ether to obtain 11.5 g (88%) of Z-D-Pip-NH2 ; m.p.: 114°-115° C., Rf2 =0.50, [α]D25 =+32.0° (c=1%, in methanol).

후처리

  1. filtrationThe separated precipitate is filtered off
  2. washthe filtrate is washed with n hydrochloric acid, n sodium hydrocarbonate solution and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue is crystallized from a mixture of ethyl acetate and ether

출처 및 근거

ORD 기록
ord-db7539b1b1a14069a917a026870485c0
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04299821

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