Triphenylphosphine → Benzyl 4-[1-(4-chloro-3-methylphenyl)-1H-tetrazol-5-yl]piperidine-1-carboxylate

HRID 1045804노트

반응식

HRID 1045804 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]2)=O)=[CH:4][C:3]=1[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C[Si]([N:65]=[N+:66]=[N-:67])(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:13][CH2:12]3)=[N:67][N:66]=[N:65]2)=[CH:4][C:3]=1[CH3:27]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 86685835Benzyl 4-[(4-chloro-3-methyl-phenyl)carbamoyl]piperidine-1-carboxylate

생성물 1

HCID 86685836Benzyl 4-[1-(4-chloro-3-methylphenyl)-1H-tetrazol-5-yl]piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The product from step A (840 mg, 2.171 mmol) and triphenylphosphine (1139 mg, 4.34 mmol) in THF (8.0 ml) was treated with diisopropylazodicarboxylate (0.844 ml, 4.34 mmol) and trimethylsilyl azide (0.574 ml, 4.34 mmol) at rt. The mixture was stirred at rt for 24 h, then quenched with aqueous saturated NaHCO3, and extracted with MTBE. The combined organic layers were concentrated. Purification of the resulting crude product on SiO2 (0 to 100% EtOAc, hexanes) afforded the title compound as a clear colorless oil. HPLC/MS: 412.2/414.1 (M+1); Rt=1.22 min (LC2).

후처리

  1. customquenched with aqueous saturated NaHCO3
  2. extractionextracted with MTBE
  3. concentrationThe combined organic layers were concentrated
  4. customPurification of the resulting crude product on SiO2 (0 to 100% EtOAc, hexanes)

출처 및 근거

ORD 기록
ord-2d8c3e79343c4082867961a545480751
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569299B2

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