Methanol → HCID 24876273, compound

HRID 1873664Notes

Reaction equation

HRID 1873664 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C@@H:9]([NH:16][C:17](=[O:19])[CH3:18])[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.[CH3:20][CH2:21][C:22](=O)[CH2:23][CH3:24].[BH4-].[Na+].CO>ClCCl.C(O)(=O)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:20][CH2:21][CH:22]([N:1]1[CH2:6][CH2:5][C:4]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C@@H:9]([NH:16][C:17](=[O:19])[CH3:18])[CH2:8][CH2:7]2)[CH2:3][CH2:2]1)[CH2:23][CH3:24]

Participants

8

Reactant 4

HCID 887MethanolHCID 7288Ethyl ketoneHCID 4311764Sodium borohydrideHCID 58966608HCID 58966608, compound

Product 1

HCID 24876273HCID 24876273, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the piperidine (B5) (20 mg, 0.077 mmol) and 3-pentanone (27 mg, 0.31 mmol) in dichloromethane (2 ml) was stirred in a vial for 90 minutes and treated with titanium (IV) isopropoxide (60 μl, 0.21 mmol) for 24 hours. To the reaction mixture was added sodium borohydride (10 mg, 0.27 mmol) and stirred for 5 hours, then treated with methanol (1 ml) and acetic acid (1 drop) for 1 hour. The solvents were evaporated and the residue was dissolved in methanol (1 ml) and acidified with TFA and purified by HPLC to give the title compound no. 56. LC-MS: m/e=329.28 (M+H). Rt=1.42 min. 1H-NMR (500 MHz, DMSO-d6): 8.65 (br.s, 1H), 8.18 (d, 1H), 7.42 (d, 1H), 7.31 (t, 1H), 7.20 (t, 1H), 7.16 (d, 1H), 4.92 (m, 1H), 3.45 (m, 1H), 3.35 (m, 1H), 3.28-3.17 (m, 2H), 3.10 (m, 1H), 2.28 (m, 2H), 2.05 (m, 1H), 1.86 (s, 3H), 1.84 (m, 4H), 1.72 (t, 1H), 1.68-1.59 (m, 2H), 1.51 (m, 1H), 1.37 (m, 1H), 0.99 (t, 5H), 0.91 (t, 1H).

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in methanol (1 ml)
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-34fb691f5537420d8a1a456cd3671dc8
Source dataset
uspto-grants-2012_11
Patent number
US08304423B2

Reaction notes

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