Sodium borohydride → Tert-butyl (5-((((trans)-2-(4-(benzyloxy)phenyl)cyclopropyl)amino)methyl)-1,3,4-oxadiazol-2-yl)carbamate

HRID 709416ノート

反応式

HRID 709416 の反応式
[CH:1]([C:3]1[O:7][C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:5][N:4]=1)=O.[B-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH2:30]([O:37][C:38]1[CH:43]=[CH:42][C:41]([C@@H:44]2[CH2:46][C@H:45]2[NH2:47])=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[BH4-].[Na+]>ClC(Cl)C>[CH2:30]([O:37][C:38]1[CH:39]=[CH:40][C:41]([C@@H:44]2[CH2:46][C@H:45]2[NH:47][CH2:1][C:3]2[O:7][C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[N:5][N:4]=2)=[CH:42][CH:43]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

参加物

6

反応物 4

HCID 4311764Sodium borohydrideHCID 23676153Sodium bis(acetyloxy)boranuidyl acetateHCID 51888238(1R,2S)-2-(4-(Benzyloxy)phenyl)cyclopropan-1-amine2 回HCID 86695278Tert-butyl (5-formyl-1,3,4-oxadiazol-2-yl)carbamate2 回

生成物 1

HCID 86695277Tert-butyl (5-((((trans)-2-(4-(benzyloxy)phenyl)cyclopropyl)amino)methyl)-1,3,4-oxadiazol-2-yl)carbamate収率 15.4%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

Tert-butyl (5-formyl-1,3,4-oxadiazol-2-yl)carbamate (Intermediate O, 220 mg, 1.041 mmol) and sodium triacetoxy borohyride (441 mg, 2.08 mmol) was added to a solution of Trans-2-[4-(benzyloxy)phenyl]cyclopropanamine (Intermediate B, 250 mg, 1.041 mmol) in dry Dichloro ethane (2.5 mL) at 0° C. and stirred at RT for 24 h, then the solvent was evaporated. The residue was taken in MeOH (2.5 mL) and NaBH4 (116 mg, 3.138 mmol) was added at 0° C. and stirred for 2 h at RT. After completion, the solvent was evaporated, the residue was taken in water (10 mL) and extracted with EtOAc (4×10 mL) Combined extracts were washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by column chromatography (SiO2) using MeOH:CHCl3 (1:99) to get tert-butyl (5-((((trans)-2-(4-(benzyloxy)phenyl)cyclopropyl)amino)methyl)-1,3,4-oxadiazol-2-yl)carbamate (70 mg, 15.3%) as pale green liquid.

後処理

  1. customthe solvent was evaporated
  2. stirringstirred for 2 h at RT
  3. customAfter completion, the solvent was evaporated
  4. extractionextracted with EtOAc (4×10 mL)
  5. washwere washed with water (10 mL), brine (10 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography (SiO2)

出典と根拠

ORDレコード
ord-4f0b6fd902da4b9f9b6e81380aefb843
出典データセット
uspto-grants-2015_11
特許番号
US09181198B2

反応ノート

読み込み中…