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

HRID 1155087

反応式

HRID 1155087 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
-20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-db7539b1b1a14069a917a026870485c0
出典データセット
uspto-grants-1981_11
特許番号
US04299821

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