Sodium triacetoxyborohydride → HCID 68708908, compound

HRID 1518226Notes

Reaction equation

HRID 1518226 reaction equation
[NH2:1][CH:2]([C:31]([O:33][CH3:34])=[O:32])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[C:6]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:5]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CCOC(C)=O>[CH:17]1([C:6]2[C:7]3[CH:8]=[CH:9][C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:12]=3[N:4]3[CH2:3][CH:2]([C:31]([O:33][CH3:34])=[O:32])[NH:1][CH2:29][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[C:5]=23)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 86637855HCID 86637855, compound

Product 1

HCID 68708908HCID 68708908, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 1-(2-amino-3-methoxy-3-oxopropyl)-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate in 1,2-DCE (0.04 M), 2 eq of NaBH(OAc)3 was added and the solution stirred overnight at RT. The reaction mixture was diluted with EtOAc. The organic phase was washed with NaHCO3 (s.s.) and brine before being dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound (quant). MS (ES+) m/z 447 (M+H)+.

Workup

  1. washThe organic phase was washed with NaHCO3 (s.s.) and brine
  2. dry with materialbefore being dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f65f190297d04b0e83463014d581069d
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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