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

HRID 1155087

Reaction equation

[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]

Participants

Conditions

Temperature: -20 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-db7539b1b1a14069a917a026870485c0
Source dataset: uspto-grants-1981_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04299821

Linked notes

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