Ammonium Acetate → Methyl 6-aminospiro[4.5]decane-7-carboxylate

HRID 539931ノート

反応式

HRID 539931 の反応式
O=[C:2]1[CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][CH2:9][CH2:8][C:3]21[CH2:7][CH2:6][CH2:5][CH2:4]2.C([O-])(=O)C.[NH4+].[BH3-]C#[N:23].[Na+]>CO>[NH2:23][CH:2]1[CH:11]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][CH2:9][CH2:8][C:3]21[CH2:7][CH2:6][CH2:5][CH2:4]2

参加物

5

反応物 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 57429459Methyl 6-oxospiro[4.5]decane-7-carboxylate

生成物 1

HCID 67973872Methyl 6-aminospiro[4.5]decane-7-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In a flask containing methyl 6-oxospiro[4.5]decane-7-carboxylate, 60, (4.10 g, 19.50 mmol) in MeOH (35 mL) was added ammonium acetate (10.52 g, 136.50 mmol) and NaCNBH3 (1.47 g, 23.40 mmol). The mixture was stirred at room temperature for 24 hrs. GCMS showed conversion to product SM (Rt=12.3 min, E+=211), product (Rt=12.6 min, ES+=212 [major] and Rt=12.45 min, ES+=212 [minor]). The solvent was evaporated, HCl (1N) was added and the aqueous phase was extracted with EtOAc. The organic phase was neutralized with NaOH (6N) to pH ˜10. The aqueous phase was extracted three times with EtOAc and twice with dichloromethane, dried over Na2SO4 to yield 1.6 g of product.

後処理

  1. customThe solvent was evaporated
  2. additionHCl (1N) was added
  3. extractionthe aqueous phase was extracted with EtOAc
  4. extractionThe aqueous phase was extracted three times with EtOAc
  5. dry with materialtwice with dichloromethane, dried over Na2SO4

出典と根拠

ORDレコード
ord-c164d8df0f2949c181db85828fbd27ad
出典データセット
uspto-grants-2014_10
特許番号
US08871774B2

反応ノート

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