Potassium Carbonate → (S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine

HRID 2251905노트

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HRID 2251905 반응식
[N:1]1([C:6]2[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=2)[CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2CN2C3C=CC=CC=3COC3C=CC=CC2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.N1CC[C@H]([OH:41])C1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:41][C@H:13]1[CH2:14][CH2:15][N:11]([CH2:10][CH2:9][C:8]2[CH:32]=[CH:33][CH:34]=[C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:7]=2)[CH2:12]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 12990604(r)-5,11-Dihydro-5-[1-(3-pyrrolidinophenethyl)pyrrolidin-2-ylmethyl]dibenzo[b,e][1,4]oxazepineHCID 22309122(S)-3-Hydroxypyrrolidine hydrochloride

생성물 1

HCID 69199429(S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
100 °C

실험 절차

3-Pyrrolidinophenethyl mesylate (1.80 g, 4.00 mmol) synthesized in Example 21, (S)-3-pyrrolidinol hydrochloride (0.50 g, 4.05 mmol) and potassium carbonate (1.70 g, 12.3 mmol) were added to acetonitrile (20 ml), and they were heated at 100° C. for 12 hours. Acetonitrile was evaporated under reduced pressure, and the residue was distributed into water and ethyl acetate. The intended product was extracted from the ethyl acetate layer with 1 M hydrochloric acid. The extract was neutralized and then the product was extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to obtain (S)-3-hydroxy-1-(3-pyrrolidinophenethyl)pyrrolidine in the form of a light yellow solid (1.04 g, 100%).

후처리

  1. customAcetonitrile was evaporated under reduced pressure
  2. extractionThe intended product was extracted from the ethyl acetate layer with 1 M hydrochloric acid
  3. extractionthe product was extracted with ethyl acetate
  4. customThe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-7e676270ee5947caa3b5646c02022d38
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320973B2

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