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

HRID 1045804ノート

反応式

HRID 1045804 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2d8c3e79343c4082867961a545480751
出典データセット
uspto-grants-2013_10
特許番号
US08569299B2

反応ノート

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