Sodium Bicarbonate → Tert-butyl 4-((((trans)-2-(4-acetamidophenyl)cyclopropyl)amino)methyl)piperidine-1-carboxylate

HRID 529336ノート

反応式

HRID 529336 の反応式
Cl.[NH2:2][C@@H:3]1[CH2:5][C@H:4]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1.[CH:16]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCl.CO>[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([C@@H:4]2[CH2:5][C@H:3]2[NH:2][CH2:16][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:20][CH2:19]2)=[CH:7][CH:8]=1)(=[O:15])[CH3:14]

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 131731922N-(4-((trans)-2-aminocyclopropyl)phenyl)acetamide, hydrochloride

生成物 1

HCID 68385184Tert-butyl 4-((((trans)-2-(4-acetamidophenyl)cyclopropyl)amino)methyl)piperidine-1-carboxylate収率 58.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of N-(4-((trans)-2-aminocyclopropyl)phenyl)acetamide, hydrochloride (150 mg, 0.662 mmol) in a mixture of dichloromethane (10 mL) and methanol (5 mL) was added tert-butyl 4-formylpiperidine-1-carboxylate (141 mg, 0.662 mmol) and stirred for 5 min, then Na(OAc)3BH (210 mg, 0.992 mmol) was added and stirred for 30 min. The crude was diluted with DCM (100 mL) and poured into sat NaHCO3 solution (50 mL). The separated organic layer was washed with water (20 mL), brine solution (20 mL) and the organic layer was dried over any sodium sulphate and concentrated. The crude was purified using silica gel (100-200 mesh) column chromatography, eluting with MeOH in DCM. Compound eluted in 4% MeOH in DCM to afford tert-butyl 4-((((trans)-2-(4-acetamidophenyl)cyclopropyl)amino)methyl)piperidine-1-carboxylate (150 mg, 0.387 mmol, 58.5% yield). LCMS (ES) m/e 387.96 (M+H), 95.06%

後処理

  1. stirringstirred for 30 min
  2. additionpoured
  3. washThe separated organic layer was washed with water (20 mL), brine solution (20 mL)
  4. dry with materialthe organic layer was dried over any sodium sulphate
  5. concentrationconcentrated
  6. customThe crude was purified
  7. washeluting with MeOH in DCM
  8. washCompound eluted in 4% MeOH in DCM

出典と根拠

ORDレコード
ord-596d0c4aecf3477b95c7cf1201da3e20
出典データセット
uspto-grants-2016_05
特許番号
US09346840B2

反応ノート

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