Pyrrolidine → 3-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1922645노트

반응식

HRID 1922645 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH3:16])([C:13]([OH:15])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:19]([CH:23]([CH3:25])C)[CH:20]([CH3:22])C.N1CCCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH3:16])([C:13]([N:19]2[CH2:20][CH2:22][CH2:25][CH2:23]2)=[O:15])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 532554551-((Tert-butoxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid

생성물 1

HCID 596056303-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-methylpyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (348 mg, 1.52 mmol) in DMF (10 mL) were added DIPEA (0.53 mL, 3.04 mmol), pyrrolidine (0.25 mL, 3.04 mmol) and HATU (693 mg, 1.82 mmol). The reaction mixture was stirred at room temperature for 18 hours and then partitioned between water and EtOAc. The organic layer was separated and washed with a 0.1N aqueous HCl solution and brine, dried over Na2SO4, filtered and concentrated to give the desired product as a white solid (334 mg, 78%). 1H NMR (400 MHz, CHCl3-d): δ 3.61-3.38 (m, 8H); 2.00-1.79 (m, 6H); 1.47-1.44 (m, 9H); 1.33 (s, 3H).

후처리

  1. custompartitioned between water and EtOAc
  2. customThe organic layer was separated
  3. washwashed with a 0.1N aqueous HCl solution and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-63fcf17a01c84a6bbb13c83d7b13da43
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173650B2

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