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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Cyclopentanecarbaldehyde → (S)-(3,5-Bistrifluoromethylbenzyl)-(1-cyclopentylmethyl-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)amine

HRID 507037
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HRID 507037 반응식
[CH:1]1([CH:6]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:8][C:9]([F:45])([F:44])[C:10]1[CH:11]=[C:12]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[CH2:13][N:14]([C:31]1[N:32]=[N:33][N:34]([CH3:36])[N:35]=1)[C@H:15]1[CH2:21][CH2:20][CH2:19][NH:18][C:17]2[CH:22]=[C:23]([C:27]([F:30])([F:29])[F:28])[C:24]([CH3:26])=[CH:25][C:16]1=2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCCl.C(Cl)Cl>[F:45][C:9]([F:8])([F:44])[C:10]1[CH:11]=[C:12]([CH:37]=[C:38]([C:40]([F:43])([F:41])[F:42])[CH:39]=1)[CH2:13][N:14]([C@H:15]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:17]2[CH:22]=[C:23]([C:27]([F:28])([F:29])[F:30])[C:24]([CH3:26])=[CH:25][C:16]1=2)[C:31]1[N:32]=[N:33][N:34]([CH3:36])[N:35]=1
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참가 물질

7

반응물 3

HCID 70106CyclopentanecarbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59432408(S)-(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amine

생성물 1

HCID 11505545(S)-(3,5-Bistrifluoromethylbenzyl)-(1-cyclopentylmethyl-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-(2-methyl-2H-tetrazol-5-yl)amine수율 70.3%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

Add cyclopentanecarboxaldehyde (462 mg, 4.71 mmol) to a solution of (S)-(3,5-bistrifluoromethylbenzyl)-(2-methyl-2H-tetrazol-5-yl)-(7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)amine (520 mg, 0.941 mmol) in acetic acid (1 mL) and 1,2-dichloroethane (10 mL) at room temperature under nitrogen and stir for 1 h. Add sodium triacetoxy borohydride (998 mg, 4.71 mmol) and stir for 5 min. Dilute the mixture with methylene chloride (30 mL) and wash with saturated aqueous sodium bicarbonate solution (2×10 mL). Extract the combined aqueous washes with methylene chloride (20 mL) and wash the combined organic extracts with brined (20 mL) and dry over anhydrous sodium sulfate. Remove the solvents under reduced pressure and purify the residue by column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:2), to provide the title compound as a colorless oil (420 mg, 70%). APCI MS m/z 635 (M+H)+.

후처리

  1. washwash with saturated aqueous sodium bicarbonate solution (2×10 mL)
  2. extractionExtract the combined aqueous washes with methylene chloride (20 mL)
  3. washwash the combined organic extracts with brined (20 mL)
  4. dry with materialdry over anhydrous sodium sulfate
  5. customRemove the solvents under reduced pressure
  6. custompurify the residue by column chromatography on silica gel
  7. washeluting with ethyl acetate/hexanes (1:2)

출처 및 근거

ORD 기록
ord-f3059f5175884d1ab973024a544eee51
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786108B2

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