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

HRID 556473

反応式

HRID 556473 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-3b507d3ac117459fb37570dde41f7ff5
出典データセット
uspto-grants-2011_11
特許番号
US08058269B2

関連ノート

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