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

HRID 556473

Reaction equation

HRID 556473 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-3b507d3ac117459fb37570dde41f7ff5
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Linked notes

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