Water → (5S)-1-(tert-Butoxycarbonyl)-5-methyl-L-proline

HRID 1412965노트

반응식

HRID 1412965 반응식
[CH3:1][C@@H:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:5]([C:14]([O:16]CC)=[O:15])[CH2:4][CH2:3]1.O.[OH-].[Li+].O>C(O)C>[C:10]([O:9][C:7]([N:6]1[C@@H:2]([CH3:1])[CH2:3][CH2:4][C@H:5]1[C:14]([OH:16])=[O:15])=[O:8])([CH3:11])([CH3:12])[CH3:13]

참가 물질

5

반응물 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 69622155(2S,5S)-1-tert-butyl 2-ethyl 5-methylpyrrolidine-1,2-dicarboxylate

생성물 1

HCID 15516206(5S)-1-(tert-Butoxycarbonyl)-5-methyl-L-proline

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of (2S,5S)-1-tert-butyl 2-ethyl 5-methylpyrrolidine-1,2-dicarboxylate (6.46 g, 25.1 mmol) in ethanol (20 mL) was added lithium hydroxide mono hydrate (2.11 g, 50.2 mmol) and deionized water (12 mL). The mixture was allowed to stir for 16 hours then partitioned between ethylacetate and a 1:1 mixture of saturated brine and 1N HCl. The aqueous layer was extracted an additional time with ethyl acetate. The organic layers were combined, dried with sodium sulfate and the solvent was removed in vacuo to yield (2S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid as a white solid (quant.) and was used directly in the following step.

후처리

  1. customthen partitioned between ethylacetate
  2. additiona 1:1 mixture of saturated brine and 1N HCl
  3. extractionThe aqueous layer was extracted an additional time with ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-61bca44570df4ea7a416ec48351d1a02
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921341B2

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