Ammonium formate → Methyl {3-[(2R)-2-aminopropyl]phenyl}acetate

HRID 1866502ノート

反応式

HRID 1866502 の反応式
Cl.[CH3:2][O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C@H:13]([NH:15][C@@H](C2C=CC=CC=2)C)[CH3:14])[CH:7]=1.C([O-])=O.[NH4+]>>[CH3:2][O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C@H:13]([NH2:15])[CH3:14])[CH:7]=1

参加物

3

反応物 2

HCID 2723923Ammonium formateHCID 46938908methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride

生成物 1

HCID 46938716Methyl {3-[(2R)-2-aminopropyl]phenyl}acetate収率 104.8%

実験手順

A solution of methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride (Preparation 26) (7.69 g, 22 mmol) and ammonium formate (6.94 g, 110 mmol) was heated to 75° C. in the presence of 20% palladium hydroxide-on-charcoal (Pd(OH)2/C, 2.00 g). After 90 minutes the reaction mixture was cooled to room temperature, filtered through arbocel and the filtrate concentrated in vacuo. The residue was partitioned between dichloromethane (100 ml) and 880 ammonia (100 ml) and the organic phase separated. The aqueous phase was extracted dichloromethane (100 ml) and the combined organic extracts dried (magnesium sulfate) and reduced in vacuo to give the title compound as a colourless oil (4.78 g). 1H NMR (400 MHz, CD3OD): δ 7.27-7.23 (1H, t), 7.13-7.09 (3H, m), 3.67 (3H, s), 3.63 (2H, s), 3.12-3.05 (1H, m), 2.67-2.57 (2H, m), 1.06 (3H, d) ppm. LRMS (electrospray): m/z [M+H]+ 208, [M+Na]+ 230.

後処理

  1. filtrationfiltered through arbocel
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was partitioned between dichloromethane (100 ml) and 880 ammonia (100 ml)
  4. customthe organic phase separated
  5. extractionThe aqueous phase was extracted dichloromethane (100 ml)
  6. dry with materialthe combined organic extracts dried (magnesium sulfate)

出典と根拠

ORDレコード
ord-dba3f4bd913f41d3b440e73d571efac2
出典データセット
uspto-grants-2009_12
特許番号
US07629358B2

反応ノート

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