Sodium borohydride → methyl 13-cyclohexyl-6-hydroxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 860744Notes

Reaction equation

HRID 860744 reaction equation
[BH4-].[Na+].[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:28]([O:30][CH3:31])=[O:29])=[CH:14][C:15]=3[N:16]3[CH2:22][C:21](=[O:23])[CH2:20][C:19]4[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=4[C:17]=23)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>CO.O1CCCC1>[CH:3]1([C:9]2[C:10]3[CH:11]=[CH:12][C:13]([C:28]([O:30][CH3:31])=[O:29])=[CH:14][C:15]=3[N:16]3[CH2:22][CH:21]([OH:23])[CH2:20][C:19]4[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=4[C:17]=23)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58765241methyl 13-cyclohexyl-6,7-dihydro-6-oxo-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

Product 1

HCID 16072721methyl 13-cyclohexyl-6-hydroxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (50 mg, 1.3 mmol) was added to a solution of methyl 13-cyclohexyl-6,7-dihydro-6-oxo -5H-indolo[2,1-a][2]benzazepine-10-carboxylate (29 mg, 0.074 mmol) in methanol (4 mL) and tetrahydrofuran (2 mL) at rt. The evolution of H2 was instantaneous and stirring was continued for 30 min at rt. The mixture was concentrated on a rotary evaporator and and the residue purified on the Shimadzu preparative liquid chromatograph. The product containing fraction was concentrated on a Speed Vac® to leave the titled compound as a white solid (27.5 mg, 96%). ESI-MS m/z 390 (MH+); 1H NMR (500 MHz, CHLOROFORM-D) □ 1.18–1.31 (m, 1 H) 1.32–1.53 (m, 2 H) 1.60–1.70 (m, 1 H) 1.71–1.84 (m, 2 H) 1.86–2.18 (m, 4 H) 2.38–3.12 (m, 3 H) 3.36–3.83 (m, 1 H) 3.94 (m, 3 H) 4.39–4.68 (m, 2 H) 7.32–7.48 (m, 4 H) 7.76 (t, J=8.39 Hz, 1 H) 7.88 (t, J=8.09 Hz, 1 H) 8.14 (m, 1 H).

Workup

  1. concentrationThe mixture was concentrated on a rotary evaporator
  2. customthe residue purified on the Shimadzu preparative liquid chromatograph
  3. additionThe product containing fraction
  4. concentrationwas concentrated on a Speed Vac®

Sources & evidence

ORD record
ord-5a4e898c602f48febb8742144b29a8a5
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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