Hydrochloric Acid → Benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 45049노트

반응식

HRID 45049 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([C:16](O)=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.Cl>C1COCC1>[OH:17][CH2:16][CH:13]1[CH2:14][CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 185384831-N-Cbz-pyrrolidine-3-carboxylic acid

생성물 1

HCID 18332648Benzyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 1-[(benzyloxy)carbonyl]pyrrolidine-3-carboxylic acid (1.0 g, 4.0 mmol) in THF (37 mL) at 0° C. was added dropwise a solution of 1.0 M borane in THF (16.4 mL). The reaction was allowed to warm to room temperature and stir for 16 hours. The mixture was cooled to 0° C. and 10% HCl (50 mL) was added. After the addition, the mixture was extracted with DCM, and the extract was washed sequentially with saturated NaHCO3 solution and brine, then dried over sodium sulfate, filtered and the solvent was removed in vacuo. The product was used without further purification in the subsequent oxidation step.

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. additionAfter the addition
  3. extractionthe mixture was extracted with DCM
  4. washthe extract was washed sequentially with saturated NaHCO3 solution and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe product was used without further purification in the subsequent oxidation step

출처 및 근거

ORD 기록
ord-1468c195fdfe40808d6fcec584e9a33e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541425B2

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