Hydrochloric Acid → (1S,5S)-5-amino-2,2-dimethylcyclohexanol hydrochloride

HRID 2280772ノート

反応式

HRID 2280772 の反応式
[OH:1][C@H:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][C@@H:4]([N:10]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:3]1.O[C@@H]1C(C)(C)CC[C@H](N2C(=O)C3C(=CC=CC=3)C2=O)C1.O.NN.[ClH:44].Cl.N[C@H]1C[C@@H](O)C(C)(C)CC1>C(O)C>[ClH:44].[NH2:10][C@@H:4]1[CH2:3][C@H:2]([OH:1])[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5]1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 712371832-((1S,3S)-3-hydroxy-4,4-dimethylcyclohexyl)isoindoline-1,3-dioneHCID 712375772-((1R,3R)-3-hydroxy-4,4-dimethylcyclohexyl)isoindoline-1,3-dioneHCID 86676353(1R,5R)-5-amino-2,2-dimethylcyclohexanol hydrochloride

生成物 1

HCID 86676351(1S,5S)-5-amino-2,2-dimethylcyclohexanol hydrochloride収率 115%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a mixture of 2-((1R,3R)-3-hydroxy-4,4-dimethylcyclohexyl)isoindoline-1,3-dione and 2-((1S,3S)-3-hydroxy-4,4-dimethylcyclohexyl)isoindoline-1,3-dione (1.1 g, 4.02 mmol) in ethanol (50 mL) was added hydrazine hydrate (0.195 mL, 4.02 mmol). The resulting solution was allowed to stir at reflux overnight under a nitrogen atmosphere. The reaction was cooled to ambient temperature and then the pH was adjusted to <2 via addition of concentrated aqueous hydrochloric acid. The precipitate was filtered off, rinsed with ethanol, and then the resulting filtrate was concentrated to 20 mL under reduced pressure. An equal volume of water was added and this mixture was stirred at ambient temperature for 15 min. The solids were filtered off, rinsed with water, and the filtrate was concentrated under reduced pressure to give a solid that was dried in a vacuum oven for a few hours to afford a mixture of (1R,5R)-5-amino-2,2-dimethylcyclohexanol hydrochloride and (1S,5S)-5-amino-2,2-dimethylcyclohexanol hydrochloride (835 mg, 4.65 mmol, 115% yield) that was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.87-8.21 (m, 3H), 2.98-3.23 (m, 1H), 2.75-3.02 (m, 1H), 1.49-1.92 (m, 2H), 1.26-1.47 (m, 3H), 0.96-1.16 (m, 1H), 0.48-0.93 (m, 6H)

後処理

  1. temperatureat reflux overnight under a nitrogen atmosphere
  2. filtrationThe precipitate was filtered off
  3. washrinsed with ethanol
  4. concentrationthe resulting filtrate was concentrated to 20 mL under reduced pressure
  5. additionAn equal volume of water was added
  6. stirringthis mixture was stirred at ambient temperature for 15 min
  7. filtrationThe solids were filtered off
  8. washrinsed with water
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto give a solid
  11. customthat was dried in a vacuum oven for a few hours
  12. customto afford

出典と根拠

ORDレコード
ord-0c138a41128b4b40a5de169227f2e13f
出典データセット
uspto-grants-2015_09
特許番号
US09139534B2

反応ノート

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