Ethyl 6-methoxy-1H-indole-2-carboxylate → Rac-6-methoxy-2,3-dihydro-1h-indole-2-carboxylic acid ethyl ester

HRID 556473

반응식

HRID 556473 반응식
C([BH3-])#N.[Na+].[CH2:5]([O:7][C:8]([C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([O:19][CH3:20])[CH:13]=2)=[O:9])[CH3:6]>C(O)(C(F)(F)F)=O>[CH2:5]([O:7][C:8]([CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][C:14]([O:19][CH3:20])=[CH:15][CH:16]=2)[NH:11]1)=[O:9])[CH3:6]

참가 물질

4

반응물 2

HCID 612959Ethyl 6-methoxy-1H-indole-2-carboxylateHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 57479057Rac-6-methoxy-2,3-dihydro-1h-indole-2-carboxylic acid ethyl ester수율 75.3%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

Sodium cyanoborohydride (750 mg, 12 mmol) (Aldrich) was added in small portions to a mixture of 6-Methoxy-1H-indole-2-carboxylic acid ethyl ester (500 mg, 2.4 mmol) (Aldrich) in TFA (10 mL), which was cooled in ice-water bath, at such a rate that gas evolution was not too vigorous. When the addition was complete, the mixture was allowed to warm to room temperature and stirred for 2.5 hr. The resulting mixture was concentrated in vacuo and the residue was dissolved in DCM. The organic layer was washed with Na2CO3 solution, dried with Na2SO4, and concentrated to give 400 mg rac-6-Methoxy-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester. MS: [M+H]+=222

후처리

  1. additionWhen the addition
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in DCM
  4. washThe organic layer was washed with Na2CO3 solution
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3b507d3ac117459fb37570dde41f7ff5
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058269B2

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