Lithium borohydride → Methyl 13-cyclohexyl-6-(hydroxymethyl)-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate

HRID 421960Notes

Reaction equation

HRID 421960 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([O:32][CH3:33])=[O:31])=[CH:12][C:13]=3[N:14]3[C:20]=2[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]([CH3:25])[CH:16]([C:26](OC)=[O:27])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[BH4-]>C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:30]([O:32][CH3:33])=[O:31])=[CH:12][C:13]=3[N:14]3[C:20]=2[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]([CH3:25])[CH:16]([CH2:26][OH:27])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 66674609Dimethyl 13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate

Product 1

HCID 66674023Methyl 13-cyclohexyl-6-(hydroxymethyl)-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-6,10-dicarboxylate was dissolved in anhydrous THF (0.05M) and LiBH4 (1 eq.) was added. The mixture was stirred at RT. After 1 h only marginal conversion to the product was observed. BH3.THF complex (1 eq.) was added and the mixture was stirred at RT. After 2h a further equivalent of BH3.THF complex was added and the mixture was stirred for 2 h. The mixture was quenched by addition of silica gel and all volatiles were evaporated in vacuo. The product was isolated by flash chromatography (PE:EtOAc, 8:2). After evaporation of the solvents the product was obtained as a colourless solid (80%). (ES+) m/z 419 (M+H)+.

Workup

  1. additionBH3.THF complex (1 eq.) was added
  2. stirringthe mixture was stirred at RT
  3. stirringthe mixture was stirred for 2 h
  4. customThe mixture was quenched by addition of silica gel
  5. customall volatiles were evaporated in vacuo
  6. customThe product was isolated by flash chromatography (PE:EtOAc, 8:2)
  7. customAfter evaporation of the solvents the product

Sources & evidence

ORD record
ord-3e8874fb9e3b40c0928c44f7308d59aa
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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