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

HRID 539931노트

반응식

HRID 539931 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c164d8df0f2949c181db85828fbd27ad
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871774B2

반응 노트

불러오는 중…