Borane → methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 860746Notes

Reaction equation

HRID 860746 reaction equation
B.[C:2]([CH:5]1[CH2:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]2=[C:16]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:17]3[CH:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:22]=3[N:7]2[CH2:6]1)(O)=[O:3]>C1COCC1>[CH:27]1([C:16]2[C:17]3[CH:18]=[CH:19][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:22]=3[N:7]3[CH2:6][CH:5]([CH2:2][OH:3])[CH2:11][C:10]4[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=4[C:8]=23)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 1607269913-cyclohexyl-10-methoxycarbonyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6-carboxylic acid

Product 1

HCID 16072734methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane in THF (0.18 mL of 1 N, 0.18 mmol) was added to a solution of methyl (±)-6-carboxy-13-cyclohexyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate (50 mg, 0.12 mmol) in THF (5 mL) at 0° C. The cooling bath was removed and stirring continued at ambient temperatures for 18 hr. The solution was diluted with ethyl acetate and washed with dilute HCl (1×), brine (3×), and then dried (Na2SO4). The crude product was 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 film (25 mg, 52%). ESI-MS m/z 404 (MH+); 1H NMR (300 MHz, MeOD) δ 1.14–2.19 (m, 11 H) 2.34–2.80 (m, 2 H) 2.82–3.26 (m, 2 H) 3.25–3.38 (m, 1 H) 3.44–3.82 (m, 1 H) 3.92 (s, 3 H) 4.48–4.61 (m, 1 H) 7.35–7.46 (m, 4 H) 7.68 (m, 1 H) 7.85 (m, 1 H) 8.17 (m, 1 H).

Workup

  1. customThe cooling bath was removed
  2. additionThe solution was diluted with ethyl acetate
  3. washwashed with dilute HCl (1×), brine (3×)
  4. dry with materialdried (Na2SO4)
  5. customThe crude product was purified on the Shimadzu preparative liquid chromatograph
  6. additionThe product containing fraction
  7. concentrationwas concentrated on a Speed Vac®

Sources & evidence

ORD record
ord-bf4ababa666e41dcac1c937995a3f9fc
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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