Sodium cyanoborohydride → HCID 59075502, compound

HRID 2307051Notes

Reaction equation

HRID 2307051 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:12]2[C:13]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20][C:14]=3[NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)[CH2:2][CH3:3].C([BH3-])#N.[Na+]>FC(F)(F)C(O)=O.CO.O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:12]2[C@@H:13]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20][C@@H:14]3[NH:15][C:16]=2[CH:17]=[CH:18][CH:19]=1)[CH2:2][CH3:3]

Participants

6

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 22396800HCID 22396800, compound

Product 1

HCID 59075502HCID 59075502, compoundYield 40.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A 0° C. solution of 10-(2-propoxyphenyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (257 mg, 0.80 mmol) in trifluoroacetic acid (4 mL) was treated with a solution of sodium cyanoborohydride (269 mg 4.28 mmol) in methanol (2 mL). The reaction was allowed to slowly warm to room temperature over 1.6 hours then diluted with water and concentrated in vacuo to remove the majority of acid. The residue was made basic with 15% NaOH, extracted twice with CH2Cl2 dried over MgSO4 and concentrated in vacuo and passed through a column of silica gel with 1:19 methanol/chloroform with 1% NH4OH to give 104 mg (40%) of a brown oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.32-7.30 (m, 1 H), 7.25 (dd, J=7.4 Hz, 1.7 Hz, 1 H), 7.11-7.07 (m, 1 H), 7.02-6.96 (m, 2 H), 6.65-6.59 (m, 1 H), 4.24-4.21 (m, 1 H), 3.97-3.84 (m, 2 H), 3.73 (dt, J=9.7 Hz, 3.3 Hz, 1 H), 3.13-3.08 (m, 1 H), 2.80-2.76 (m, 1 H), 2.73-2.67 (m, 1 H), 2.47-2.41 (m, 1 H), 2.06-2.04 (m, 1 H), 1.95-1.92 (m, 1 H), 1.75-1.70 (m, 2 H), 1.59-1.55 (m, 1 H), 1.37-1.34 (m, 1 H) 0.95 (t, J=7.4 Hz, 3 H); HRMS (FAB) calcd for C21H26N2O+H1: 323.2123 found 323.2116.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the majority of acid
  3. extractionextracted twice with CH2Cl2
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf3f7022875f45b3811e5f8033b95148
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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