(R)-Methyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine → HCID 67509785, compound

HRID 1054098Notes

Reaction equation

HRID 1054098 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][N:7]=2)=[CH:2]1.[CH:14]1([Mg]Br)[CH2:16][CH2:15]1>>[CH:14]1([CH:10]([C:9]2[CH:8]=[N:7][C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[CH:13][CH:12]=2)[OH:11])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 2764563(R)-Methyl-(5,6,7,8-tetrahydro-quinolin-8-yl)-amineHCID 178418630HCID 178418630, compound

Product 1

HCID 67509785HCID 67509785, compound

Procedure

Synthesized using compound 56b (270 mg, 1.43 mmol) and cyclopropylmagnesium bromide (5.72 mL, 2.86 mmol, 0.5 M in THF) according to Method D. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (1:1) as eluent. Yellow solid. Yield: 138 mg, 42%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.37-0.45 (m, 1H), 0.50 (dq, J=9.7, 4.8 Hz, 1H), 0.57-0.71 (m, 2H), 1.18-1.29 (m, 1H), 2.48 (br. s., 1H), 4.06 (d, J=8.2 Hz, 1H), 7.39 (dd, J=5.0, 3.2 Hz, 1H), 7.60 (dd, J=8.2, 0.6 Hz, 1H), 7.64-7.68 (m, 1H), 7.78-7.85 (m, 1H), 7.89 (dd, J=3.0, 1.4 Hz, 1H), 8.60-8.64 (m, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=2.8, 3.6, 19.1, 76.1, 120.0, 123.4, 126.2, 126.3, 134.5, 137.2, 141.9, 147.6, 152.8; (ESI): m/z=232.26 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (1:1) as eluent

Sources & evidence

ORD record
ord-d6d14af57de94c91b6e9eb970e5ddbd5
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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