3-Butyl-8-azabicyclo[3,2,1]octane → HCID 68915759, compound

HRID 969396Notes

Reaction equation

HRID 969396 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]([CH2:11][C@H:12]([CH3:15])[CH2:13]I)[C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[CH2:18]([CH:22]1[CH2:28][CH:27]2[NH:29][CH:24]([CH2:25][CH2:26]2)[CH2:23]1)[CH2:19][CH2:20][CH3:21]>CC#N>[CH2:18]([CH:22]1[CH2:23][CH:24]2[N:29]([CH2:13][C@@H:12]([CH3:15])[CH2:11][N:6]3[C:5]4[CH:16]=[CH:17][C:2]([F:1])=[CH:3][C:4]=4[O:9][CH2:8][C:7]3=[O:10])[CH:27]([CH2:26][CH2:25]2)[CH2:28]1)[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 689079663-Butyl-8-azabicyclo[3,2,1]octaneHCID 68915302HCID 68915302, compound

Product 1

HCID 68915759HCID 68915759, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A microwave vial was charged with (S)-7-fluoro-4-(3-Iodo-2-methylpropyl)-4H-benzo[1,4]oxazin-3-one (111MF20) (0.047 g, 0.13 mmol) and 3-butyl-8-azabicyclo[3,2,1]octane (0.039 g, 0.23 mmol) in MeCN (2 mL) and sealed. After microwave irradiation, 100° C., 60 min, the reaction mixture was purified by cation exchange CC followed by flash CC (SiO2; CH2Cl2/MeOH 50:1) to give the title compound (112KK05) (0.017 g, 33%). 1H NMR (CD3OD) δ 7.34-7.30 (m, 1H), 6.80-6.75 (m, 2H), 4.61 (ABq, J=18.8 Hz, J=15.1 Hz, CH2), 4.04 (dd, J=14.3 Hz, J=5.9 Hz, 1H), 3.93 (dd, J=14.3 Hz, J=8.2 Hz, 1H), 3.18-3.10 (m, 2H), 2.36-2.23 (m, 2H), 2.03-1.85 (m, 3H), 1.62-1.45 (m, 5H), 1.36-1.14 (m, 8H), 0.92-0.87 (m, 2 CH2); 13C NMR (CD3OD) δ 166.2, 160.4 (d, J=242.3 Hz), 148.1 (d, J=11.9 Hz), 126.3 (d, J=2.9 Hz), 118.1 (d, J=9.7 Hz), 109.8 (d, J=22.9 Hz), 105.7 (d, J=26.5 Hz), 68.6, 62.5, 61.2, 58.3, 46.4, 39.0, 37.9, 32.1, 30.2, 29.0, 27.8, 27.2, 23.9, 17.2, 14.4.

Workup

  1. customsealed
  2. customAfter microwave irradiation, 100° C., 60 min
  3. customthe reaction mixture was purified by cation exchange CC

Sources & evidence

ORD record
ord-50290b4465284ab0a0fc717e44caf3b8
Source dataset
uspto-grants-2007_12
Patent number
US07307075B2

Reaction notes

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